Dichloromethane → HCID 53703072, compound

HRID 1732824Notes

Reaction equation

HRID 1732824 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+:35]([O-:37])=[O:36])=[C:28]([CH:32]=[CH:33][CH:34]=1)[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][CH:34]=[C:26]([OH:25])[C:27]=1[N+:35]([O-:37])=[O:36]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10868DicyclohexylcarbodiimideHCID 2932913-Hydroxy-2-nitrobenzoic acidHCID 853477Methyl L-prolinate

Product 1

HCID 53703072HCID 53703072, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

12.9 g of L-proline methyl ester and 21.0 g of N,N'-dicyclohexylcarbodiimide were successively added to an ice-cooled and constantly stirred solution of 18.3 g of 3-hydroxy-2-nitrobenzoic acid dissolved in a mixture consisting of 360 ml of dichloromethane and 30 ml of N,N'-dimethylformamide, and then the same treatment as in Example 1 was carried out. Thus, there was obtained 24.2 g of 1-(3-hydroxy-2-nitrobenzoyl)-L-proline methyl ester as a yellow-colored needle-like crystal having a melting point of 114° to 116° C.

Workup

  1. temperaturecooled

Sources & evidence

ORD record
ord-6118d94416024cfba2c4d589187df885
Source dataset
uspto-grants-1980_12
Patent number
US04239683

Reaction notes

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