Dichloromethane → 1-(3-hydroxy-4-methoxy-2-nitrobenzoyl)-L-proline methyl ester

HRID 1732825Notes

Reaction equation

HRID 1732825 reaction equation
[CH3:1][O:2][C:3](=[O:9])[C@@H:4]1[CH2:8][CH2:7][CH2:6][NH:5]1.C1(N=C=NC2CCCCC2)CCCCC1.[OH:25][C:26]1[C:27]([N+:37]([O-:39])=[O:38])=[C:28]([CH:32]=[CH:33][C:34]=1[O:35][CH3:36])[C:29](O)=[O:30].ClCCl>CN(C=O)C>[CH3:1][O:2][C:3](=[O:9])[C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:29](=[O:30])[C:28]1[CH:32]=[CH:33][C:34]([O:35][CH3:36])=[C:26]([OH:25])[C:27]=1[N+:37]([O-:39])=[O:38]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10868DicyclohexylcarbodiimideHCID 853477Methyl L-prolinateHCID 129541683-Hydroxy-4-methoxy-2-nitrobenzoic acid

Product 1

HCID 545437951-(3-hydroxy-4-methoxy-2-nitrobenzoyl)-L-proline methyl esterYield 73.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6.5 g of L-proline methyl ester and 10.5 g of N,N'-dicyclohexylcarbodiimide were successively added to an ice-cooled and constantly stirred solution of 10.7 g of 3-hydroxy-4-methoxy-2-nitrobenzoic acid dissolved in a mixture consisting of 180 ml of dichloromethane and 15 ml of N,N'-dimethylformamide, and then the same treatment as in Example 1 was carried out. Thus, there was obtained 12 g of 1-(3-hydroxy-4-methoxy-2-nitrobenzoyl)-L-proline methyl ester as a yellow-colored prismatic crystal having melting point of 108° to 110° C.

Workup

  1. temperaturecooled

Sources & evidence

ORD record
ord-8f8d2fc6fcdc45e5a256104945c7da35
Source dataset
uspto-grants-1980_12
Patent number
US04239683

Reaction notes

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