Water → D-2-Amino-5-phenyl-pentanoic acid

반응식

O[C@@H](C1C=CC=CC=1)[C@@H](N(C)[C:6](=[O:18])[C@H:7]([NH2:17])[CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)C.[OH2:26]>>[NH2:17][C@H:7]([CH2:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:6]([OH:18])=[O:26]

참가 물질

반응물 2

HCID 962Water2회

HCID 536999852(R)-Amino-5-phenyl-pentanoic acid (2(S)-hydroxy-1(S)-methyl-2-phenyl-ethyl)-methyl-amide

생성물 1

HCID 6993756D-2-Amino-5-phenyl-pentanoic acid

실험 절차

A solution of the compound of Example 199, Step A (400 mg, 1.18 mmol) in water (10 mL) was heated to reflux for 20 h. The reaction was diluted with water (20 mL) and extracted with CH2Cl2 (2×20 mL). The combined organic extracts were back extracted with water (2×20 mL) and the combined aqueous extracts were concentrated down to a white solid. The solid was triturated with EtOH to remove residual pseudoephedrine and deliver Example 199, Step B (135 mg, 60%): +APcI MS (M+1)+ 194.

후처리

temperatureto reflux for 20 h
extractionextracted with CH2Cl2 (2×20 mL)
extractionThe combined organic extracts were back extracted with water (2×20 mL)
concentrationthe combined aqueous extracts were concentrated down to a white solid
customThe solid was triturated with EtOH
customto remove residual pseudoephedrine

출처 및 근거

ORD 기록: ord-13b940db366c458e9353f903abe554c2
출처 데이터셋: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US06953791B2

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