Sodium Hydroxide → [4-Azidomethyl-2-phenylbenzoyl]methionine methyl ester

HRID 2121244Notes

Reaction equation

HRID 2121244 reaction equation
CO[C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]=[N+:12]=[N-:13])=[CH:6][C:5]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-].[Na+].Cl.[CH3:24][O:25][C:26](=[O:33])[C@H:27]([CH2:29][CH2:30][S:31][CH3:32])[NH2:28].Cl.COC(=O)[C@H](CCSC)NC(=O)C1C=CC(N)=CC=1C1C=CC=CC=1>CO>[CH3:24][O:25][C:26](=[O:33])[C@H:27]([CH2:29][CH2:30][S:31][CH3:32])[NH:28][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]=[N+:12]=[N-:13])=[CH:6][C:5]=1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 11435579L-Methionine, methyl ester, hydrochlorideHCID 544461164-Azidomethyl-2-phenylbenzoic acid methyl esterHCID 69612387(4-Amino-2-phenylbenzoyl)methionine methyl ester hydrochloride

Product 1

HCID 20622822[4-Azidomethyl-2-phenylbenzoyl]methionine methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The desired compound was prepared by saponification of the product of Example 332A using sodium hydroxide in refluxing aqueous methanol, followed by coupling of the resulting acid with methionine methyl ester hydrochloride using the procedure of step C in the preparation of compound 8.

Sources & evidence

ORD record
ord-0b18c96f3a2040a3b3e3a38bc9362c6d
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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