2-{[(3-Methylphenyl)carbamoyl]amino}acetic acid → HCID 19968145, compound

HRID 975971Notes

Reaction equation

HRID 975971 reaction equation
[CH3:1][N:2]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:3](=[O:15])[CH:4]1[CH2:8][CH2:7][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:5]1.[CH3:22][C:23]1[CH:24]=[C:25]([NH:29][C:30](=[O:36])[NH:31][CH2:32][C:33](O)=[O:34])[CH:26]=[CH:27][CH:28]=1>ClCCCl>[CH3:1][N:2]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:3](=[O:15])[CH:4]1[CH2:8][CH2:7][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]1[C:33](=[O:34])[CH2:32][NH:31][C:30]([NH:29][C:25]1[CH:26]=[CH:27][CH:28]=[C:23]([CH3:22])[CH:24]=1)=[O:36]

Participants

4

Reactant 2

HCID 149969602-{[(3-Methylphenyl)carbamoyl]amino}acetic acidHCID 19968220HCID 19968220, compound

Product 1

HCID 19968145HCID 19968145, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

By proceeding in a fashion similar to that described in Example 1, but starting from 1.2 g of (2RS,5SR)-N-methyl-N-phenyl-5-phenylprolinamide, 0.94 g of 2-[3-(3-methylphenyl)ureido]acetic acid in suspension in 25 cm3 of 1,2-dichloroethane and 0.33 cm3 of sulphinyl chloride, after recrystallization in acetonitrile, 1 g of (2RS,5SR)-N-methyl-1-[3-(3-methylphenyl)ureidoacetyl]-N-phenyl-5-phenylprolinamide, melting at 210° C., is obtained.

Workup

  1. custom0.33 cm3 of sulphinyl chloride, after recrystallization in acetonitrile

Sources & evidence

ORD record
ord-86b3750d401a4989b801fb807f732077
Source dataset
uspto-grants-1997_03
Patent number
US05610144

Reaction notes

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