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

HRID 1976953ノート

反応式

HRID 1976953 の反応式
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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fcb6fa55b6b544bebe93d68d62474baa
出典データセット
uspto-grants-2001_05
特許番号
US06229011B1

反応ノート

読み込み中…