(R)-(+)-1-苯丙胺 → (R)-1-(benzyloxycarbonylamino)-2-methylpropylphosphonous acid

HRID 490932

反应方程式

HRID 490932 反应方程式
[CH2:1]([O:8][C:9]([NH:11][CH:12]([P:16]([OH:18])[OH:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC[C@@H](N)C1C=CC=CC=1>C(O)C.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([P:16]([OH:17])[OH:18])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参与物

5

反应物 2

HCID 5324978(R)-(+)-1-苯丙胺HCID 213258521-Carbobenzyloxyamino-2-methylpropanephosphonous acid

产物 1

HCID 67375324(R)-1-(benzyloxycarbonylamino)-2-methylpropylphosphonous acid收率 32.4%

试剂、催化剂与溶剂 2

HCID 702乙醇溶剂HCID 8857乙酸乙酯溶剂

实验过程

A solution of 1-(benzyloxycarbonylamino)-2-methylpropylphosphonous acid (3.4 g, 12.5 mmol) in 20 mL of absolute ethanol was heated to reflux and (R)-(+)-methylbenzylamine (96% ee, 1.5 g, 12.5 mmol) was added. The resulting mixture was diluted with 120 mL of ethyl acetate. The precipitate was filtered off, washed with 100 mL of ethyl acetate and 100 mL of ether, dried in vacuo to afford (R)-1-(benzyloxycarbonylamino)-2-methylpropylphosphonous acid as a white solid (1.1 g) with a rotation [α]D=−10.87° (c=10 mg/mL 9:1 DMF-H2O). This material was found to be 93% ee by chiral HPLC.

后处理

  1. temperatureto reflux
  2. filtrationThe precipitate was filtered off
  3. washwashed with 100 mL of ethyl acetate and 100 mL of ether
  4. customdried in vacuo

来源与证据

ORD记录
ord-038668abce88414ba18426d9f343faca
来源数据集
uspto-grants-2009_05
专利号
US07528173B2

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