Hydroxide → HCID 9850091, compound

HRID 2270859Notes

Reaction equation

HRID 2270859 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:26]=[C:25]([C:27]([NH:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([O:37]C(C3C=CSC=3)=O)[CH:32]=2)=[O:28])[CH:24]=[C:23]([Cl:45])[C:5]=1[C:6]([NH:8][C@H:9]([C:19]([O:21]C)=[O:20])[CH2:10][NH:11][C:12]([C:14]1[CH:18]=[CH:17][S:16][CH:15]=1)=[O:13])=[O:7].[OH-].S1C=CC(C(NC[C@@H](C(OC)=O)N)=O)=C1>CO>[Cl:3][C:4]1[CH:26]=[C:25]([C:27]([NH:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([OH:37])[CH:32]=2)=[O:28])[CH:24]=[C:23]([Cl:45])[C:5]=1[C:6]([NH:8][C@H:9]([C:19]([OH:21])=[O:20])[CH2:10][NH:11][C:12]([C:14]1[CH:18]=[CH:17][S:16][CH:15]=1)=[O:13])=[O:7]

Participants

6

Reactant 4

HCID 961HydroxideHCID 14798Sodium HydroxideHCID 131723043HCID 131723043, compoundHCID 131723044HCID 131723044, compound

Product 1

HCID 9850091HCID 9850091, compoundYield 130.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

An aqueous solution of sodium hydroxide (1 M; 0.305 mL, 0.305 mmol) was added to a solution of N-[2,6-dichloro-4-[[[[3-[(thiophene-3-carbonyl)oxy]phenyl]methy]amino]carbonyl]benzoyl]-3-[(thiophene-3-carbonyl)amino]-L-alanine, methyl ester (101 mg, 0.153 mmol) in methanol (2 mL). The solution was allowed to stir overnight and then concentrated. An aqueous solution of odium hydroxide (1 M; 0.210 mL, 0.210 mmol) was added to a solution of N-[2,6-dichloro-4-[[(3-hydroxyphenyl)methyl]amino]carbonyl]benzoyl]-3-[(thiophene-3-carbonyl)amino]-L-alanine, methyl ester (58 mg, 0.105 mmol) in methanol (2 mL). The solution was allowed to stir overnight and then concentrated. The residues from the two reactions were purified by HPLC and lyophilized to give N-[2,6-dichloro-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl)benzoyl]-3-[(thiophene-3-carbonyl)amino]-L-alanine (107 mg, 78%) as a white solid.

Workup

  1. concentrationconcentrated
  2. stirringto stir overnight
  3. concentrationconcentrated
  4. customThe residues from the two reactions were purified by HPLC

Sources & evidence

ORD record
ord-556fbd31ce20457aa5e130017f8df5fe
Source dataset
uspto-grants-2001_12
Patent number
US06331640B1

Reaction notes

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