50890-96-5 N-甲氧羰基-D-苯甘氨酸

中文名称: N-甲氧羰基-D-苯甘氨酸
英文名称: N-Methoxycarbonyl-D-phenylglycine
CAS号
分子式: C₁₀H₁₁NO₄
分子量: 209.2
更新日期: 2026-06-23

名称和标识

中文名: N-甲氧羰基-D-苯甘氨酸
英文名: N-Methoxycarbonyl-D-phenylglycine
CAS号: 50890-96-5
分子式: C10H11NO4
分子量: 209.2
中文别名: MOC-D-苯甘胺酸; (R)-2-(甲氧羰基氨基)-2-苯基乙酸; MOC-D-苯甘氨酸; (ALPHAR)-ALPHA-[(甲氧羰基)氨基]苯乙酸; MOC-D-苯甘; (R)-2-(甲氧基甲酰胺基)-2-苯基乙酸; (R)-2-(甲氧羰基氨基)-2-苯乙酸
英文别名: (R)-2-(methoxycarbonylamino)-2-phenylacetic acid; Moc-D-Phg-OH; (R)-2-(Methoxycarbonylamino)-2-phenylethanoic acid; (alphaR)-alpha-[(Methoxycarbonyl)amino]benzeneacetic acid; (2R)-2-[(methoxycarbonyl)amino]-2-phenylacetic acid; Moc-D-Phg; Benzeneacetic acid, a-[(methoxycarbonyl)amino]-, (aR)-; (R)-Methoxy-carbonylamino-phenyl-acetic acid; (R)-2-((methoxycarbonyl)amino)-2-phenylacetic acid; [(Methoxycarbonyl)amino](phenyl)acetic acid

物化属性

Log S (ESOL): -1.88
LogP: 1.52
PSA: 75.63 Å²
外观: 白色或类白色结晶性粉末至晶体，对空气敏感
密度: 1.3±0.1 g/cm³
折射率: 1.551
旋光度: [α]20/D +4±1º (c=1)
沸点: 391.3±35.0 °C (760 mmHg)
溶解度: 2.77 mg/ml ; 0.0132 mol/l
熔点: 117-121℃
精确质量: 209.068802
蒸汽压: 0.0±0.9 mmHg (25°C)
酸度系数(pKa): 3.96±0.10
闪点: 190.5±25.9 °C

安全信息

安全说明

运输信息：常温运输。危险描述：非危险化学品。

生产及用途

用途与制备

化学合成；是一种甘氨酸衍生物

化学合成

合成路线 1（1. 合成：50890-96-5）

步骤：在0℃下，向D-苯基甘氨酸（10.0g，66.1mmol）和NaOH（21.2g，265mmol）的水（60mL）溶液中，在20分钟内滴加氯甲酸甲酯（10.2mL，133mmol）。将所得反应在0℃下搅拌1小时，然后使用浓盐酸（25mL，300mmol）酸化。酸性溶液用EtOAc（3×100mL）萃取，合并的有机物用MgSO₄干燥，过滤并真空浓缩，得到Int-2a（12.6g，91％），其无需进一步纯化即可使用。
条件：With sodium hydroxide In water at 0℃; for 1.33 h
收率：91%
参考文献：[1] Patent: WO2010/132538, 2010, A1. Location in patent: Page/Page column 102-103 [2] Patent: WO2011/87740, 2011, A1. Location in patent: Page/Page column 73; 74 [3] Patent: WO2012/40923, 2012, A1. Location in patent: Page/Page column 71 [4] Patent: WO2012/50848, 2012, A1. Location in patent: Page/Page column 70-71 [5] Patent: WO2012/125926, 2012, A2. Location in patent: Page/Page column 34 [6] Patent: WO2013/39876, 2013, A1. Location in patent: Page/Page column 62-63 [7] Patent: WO2013/39878, 2013, A1. Location in patent: Page/Page column 58; 59 [8] Patent: EP2513113, 2018, B1. Location in patent: Paragraph 0288; 0290; 0291 [9] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 3, p. 255 - 258 [10] European Journal of Medicinal Chemistry, 2015, vol. 101, p. 163 - 178 [11] European Journal of Medicinal Chemistry, 2017, vol. 125, p. 87 - 100 [12] Patent: KR2017/31307, 2017, A. Location in patent: Paragraph 0169-0171 [13] RSC Advances, 2018, vol. 8, # 55, p. 31803 - 31821 [14] Patent: US2015/166514, 2015, A1. Location in patent: Paragraph 0177 [15] Patent: US2012/230951, 2012, A1. Location in patent: Page/Page column 115 [16] Patent: WO2010/138791, 2010, A1. Location in patent: Page/Page column 75 [17] Patent: WO2010/138790, 2010, A1. Location in patent: Page/Page column 39-40 [18] Patent: WO2011/54834, 2011, A1. Location in patent: Page/Page column 50 [19] Patent: WO2012/41227, 2012, A1. Location in patent: Page/Page column 64 [20] Patent: WO2012/41014, 2012, A1. Location in patent: Page/Page column 80-81 [21] Patent: WO2012/40924, 2012, A1. Location in patent: Example 2 [22] Patent: US2012/219594, 2012, A1 [23] Patent: EP2545060, 2015, B1. Location in patent: Paragraph 0230; 0231

合成路线 2（2. 合成：50890-96-5）

步骤：在7分钟内将TFA（16mL）滴加到上述产物的冷却（冰/水）CH₂Cl₂（160mL）溶液中，除去冷却浴并将反应混合物搅拌20小时。由于脱保护仍未完成，因此加入另外的TFA（1.0mL）并继续搅拌另外2小时。真空除去挥发性组分，将得到的油状残余物用乙醚（15mL）和己烷（12mL）处理，得到沉淀物。过滤沉淀物，用乙醚/己烷（~1：3比例; 30mL）洗涤，真空干燥，得到蓬松的白色固体状的Cap-4（5.57g）。旋光度：-176.9°[c = 3.7 mg / mL，在H₂O中; λ= 589nm下]。1H NMR（DMSO-d6，δ= 2.5ppm，400MHz）：δ12.84（br s，1H），7.96（d，J = 8.3,1H），7.41-7.29（m，5H），5.14（d，J = 8.3,1H），3.55（s，3H）。LC（条件I）：RT = 1.01min; > 95％同质性指数; LC / MS：。计算。对于[M + H] + C₁₀H₁₂NO₄⁺ 210.08;发现210.17; HRMS：。计算。[M + H] + C₁₀H₁₂NO₄的产率210.0766;发现210.0756。
条件：With trifluoroacetic acid In dichloromethane for 22 h; Cooling with ice
收率：5.57 g
参考文献：[1] Patent: US2009/233925, 2009, A1. Location in patent: Page/Page column 20 [2] Patent: WO2010/17401, 2010, A1. Location in patent: Page/Page column 188 [3] Patent: WO2010/120621, 2010, A1. Location in patent: Page/Page column 85; 86 [4] Patent: WO2010/138488, 2010, A1. Location in patent: Page/Page column 79-80 [5] Patent: WO2010/138368, 2010, A1. Location in patent: Page/Page column 38-39 [6] Patent: WO2011/60000, 2011, A1. Location in patent: Page/Page column 124-125 [7] Patent: WO2011/59850, 2011, A1. Location in patent: Page/Page column 40 [8] Patent: WO2011/75439, 2011, A1. Location in patent: Page/Page column 35 [9] Patent: WO2012/18325, 2012, A1. Location in patent: Page/Page column 37-38 [10] Patent: WO2012/39717, 2012, A1. Location in patent: Page/Page column 185-186 [11] Patent: EP2328865, 2017, B1. Location in patent: Paragraph 0340; 0342 [12] Patent: US2008/44379, 2008, A1. Location in patent: Page/Page column 35 [13] Patent: US2008/44380, 2008, A1. Location in patent: Page/Page column 34 [14] Patent: WO2008/144380, 2008, A1. Location in patent: Page/Page column 49 [15] Patent: WO2009/102318, 2009, A1. Location in patent: Page/Page column 45 [16] Patent: US2010/249190, 2010, A1. Location in patent: Page/Page column 28-29 [17] Patent: WO2010/117635, 2010, A1. Location in patent: Page/Page column 158

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