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

HRID 1976953Notes

Reaction equation

HRID 1976953 reaction equation
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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-fcb6fa55b6b544bebe93d68d62474baa
Source dataset
uspto-grants-2001_05
Patent number
US06229011B1

Reaction notes

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