Acetyl chloride → 3-amino-N-[2,6-dichloro-4-[[[(3-hydroxyphenyi)methyl]amino]carbonyl]benzoyl]-L-alanine, methyl ester hydrochloride

HRID 393060Notes

Reaction equation

HRID 393060 reaction equation
C([Cl:4])(=O)C.[Cl:5][C:6]1[CH:28]=[C:27]([C:29]([NH:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([OH:39])[CH:34]=2)=[O:30])[CH:26]=[C:25]([Cl:40])[C:7]=1[C:8]([NH:10][C@H:11]([C:21]([O:23][CH3:24])=[O:22])[CH2:12][NH:13]C(OC(C)(C)C)=O)=[O:9]>CO>[ClH:4].[NH2:13][CH2:12][C@@H:11]([C:21]([O:23][CH3:24])=[O:22])[NH:10][C:8](=[O:9])[C:7]1[C:6]([Cl:5])=[CH:28][C:27]([C:29]([NH:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([OH:39])[CH:34]=2)=[O:30])=[CH:26][C:25]=1[Cl:40]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 131723029N-[2,6-dichloro-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]benzoyl]-3-[[(1,1-dimethylethoxy)carbonyl]amino]-L-alanine, methyl ester

Product 1

HCID 1317230303-amino-N-[2,6-dichloro-4-[[[(3-hydroxyphenyi)methyl]amino]carbonyl]benzoyl]-L-alanine, methyl ester hydrochlorideYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of acidic methanol was prepared by adding acetyl chloride (25 mL, 351.6 mmol) to cooled (˜0° C.) methanol (200 mL) and stirring for 10 min. This solution was added to N-[2,6-dichloro-4-[[[(3-hydroxyphenyl)methyl]amino]-carbonyl]benzoyl]-3-[[(1,1-dimethylethoxy) carbonyl]amino]-L-alanine, methyl ester (8.64 g, 16.0 mmol) and the resulting solution was stirred at room temperature for 16 h. The solvent was evaporated to give 3-amino-N-[2,6-dichloro-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]benzoyl]-L-alanine, methyl ester hydrochloride (7.40 g, 97%) as a cream-colored foam.

Workup

  1. stirringthe resulting solution was stirred at room temperature for 16 h
  2. customThe solvent was evaporated

Sources & evidence

ORD record
ord-4e8dfe9604264d75815acc7f8ae98c1a
Source dataset
uspto-grants-2004_10
Patent number
US06803384B2

Reaction notes

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