Lithium Hydroxide → N-[[2-chloro-4-[[(3-hydroxyphenyl)amino]carbonyl]phenyl]carbonyl]-4-[[(2,6-dichlorophenyl)carbonyl]amino]-L-phenylalanine

HRID 1976953노트

반응식

HRID 1976953 반응식
C[O:2][C:3](=[O:43])[C@H:4]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:33]([C:35]2[C:40]([Cl:41])=[CH:39][CH:38]=[CH:37][C:36]=2[Cl:42])=[O:34])=[CH:28][CH:27]=1)[NH:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=2)=[O:15])=[CH:10][C:9]=1[Cl:24])=[O:7].[OH-].[Li+]>CO.O1CCCC1>[Cl:24][C:9]1[CH:10]=[C:11]([C:14]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=2)=[O:15])[CH:12]=[CH:13][C:8]=1[C:6]([NH:5][C@H:4]([C:3]([OH:43])=[O:2])[CH2:25][C:26]1[CH:27]=[CH:28][C:29]([NH:32][C:33]([C:35]2[C:36]([Cl:42])=[CH:37][CH:38]=[CH:39][C:40]=2[Cl:41])=[O:34])=[CH:30][CH:31]=1)=[O:7]

참가 물질

5

반응물 2

HCID 3939Lithium HydroxideHCID 54181036N-[[2-chloro-4-[[(3-hydroxyphenyl)amino]carbonyl]phenyl]carbonyl]-4-[[(2,6-dichlorophenyl)carbonyl]amino]-L-phenylalanine methyl ester

생성물 1

HCID 54199832N-[[2-chloro-4-[[(3-hydroxyphenyl)amino]carbonyl]phenyl]carbonyl]-4-[[(2,6-dichlorophenyl)carbonyl]amino]-L-phenylalanine수율 87.3%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of N-[[2-chloro-4-[[(3-hydroxyphenyl)amino]carbonyl]phenyl]carbonyl]-4-[[(2,6-dichlorophenyl)carbonyl]amino]-L-phenylalanine methyl ester (35 mg; 0.053 mmol) in methanol (0.35 mL) and tetrahydrofuran (0.35 mL) was treated with an aqueous 1N lithium hydroxide solution (0.16 mL) and the mixture was stirred at room temperature under argon for 90 minutes. The solution was concentrated under reduced pressure, then was diluted with water (5 mL) and extracted with diethyl ether (2×5 mL). The separated aqueous layer was acidified with 1 N HCl (0.18 mL) and the resulting colorless solid was filtered off, washed with water, and dried to give 29 mg of N-[[2-chloro-4-[[(3-hydroxyphenyl)amino]carbonyl]phenyl]carbonyl]-4-[[(2,6-dichlorophenyl)carbonyl]amino]-L-phenylalanine. FAB HRMS: (C31H24Cl3N3O6) Obs. Mass 640.0821 Calcd. Mass 640.0809 (M+H).

후처리

  1. concentrationThe solution was concentrated under reduced pressure
  2. additionwas diluted with water (5 mL)
  3. extractionextracted with diethyl ether (2×5 mL)
  4. filtrationthe resulting colorless solid was filtered off
  5. washwashed with water
  6. customdried

출처 및 근거

ORD 기록
ord-fcb6fa55b6b544bebe93d68d62474baa
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06229011B1

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