Methanol → 3-[[(S)-2-amino-1-oxo-3-phenylpropyl]amino]propanoic acid, phenylmethyl ester, hydrochloride

HRID 1088606ノート

反応式

HRID 1088606 の反応式
CC(C)(OC([NH:7][C@@H:8]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:9]([NH:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])=[O:10])=O)C.C(Cl)(Cl)[Cl:33].CO>Cl.C(O)(=O)C>[ClH:33].[NH2:7][C@@H:8]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:9]([NH:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:15])=[O:10]

参加物

6

反応物 3

HCID 887MethanolHCID 6212ChloroformHCID 136862023-[[(S)-2-[[(1,1-Dimethylethoxy)carbonyl]amino]-1-oxo-3-phenylpropyl]amino]propanoic acid, phenylmethyl ester

生成物 1

HCID 694622273-[[(S)-2-amino-1-oxo-3-phenylpropyl]amino]propanoic acid, phenylmethyl ester, hydrochloride

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒2 回HCID 313Hydrochloric Acid溶媒

実験手順

A solution of the phenylmethyl ester product from part (a) (13.65 g., 32 mmole) in 1.5N hydrogen chloride gas in acetic acid solution (90 ml.) is stirred for 90 minutes at room temperature, and then the solvent is evaporated in vacuo. The residue is triturated in ether and the resulting white precipitate is collected to give 11.45 g. of crude product as a powdery white solid; m.p. 169°-175°. TLC (silica gel; chloroform:methanol:acetic acid, 6:1:1) Rf =0.52. One recrystallization from acetonitrile gives an analytical sample of 3-[[(S)-2-amino-1-oxo-3-phenylpropyl]amino]propanoic acid, phenylmethyl ester, hydrochloride as white needles; m.p. 170.5°-175°.

後処理

  1. customthe solvent is evaporated in vacuo
  2. customThe residue is triturated in ether
  3. customthe resulting white precipitate is collected
  4. customto give 11.45 g
  5. customOne recrystallization from acetonitrile

出典と根拠

ORDレコード
ord-7aaa0c2d2a1b42e9971aabc10cd0525b
出典データセット
uspto-grants-1990_10
特許番号
US04963539

反応ノート

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