2-{[(3-Methylphenyl)carbamoyl]amino}acetic acid → HCID 131719903, compound

HRID 975950Notes

Reaction equation

HRID 975950 reaction equation
[C:1]1([CH:7]2[NH:11][CH:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:17][C:18]1[CH:19]=[C:20]([NH:24][C:25](=[O:31])[NH:26][CH2:27][C:28](O)=[O:29])[CH:21]=[CH:22][CH:23]=1>ClCCCl.S(Cl)(Cl)=O>[CH3:17][C:18]1[CH:19]=[C:20]([NH:24][C:25](=[O:31])[NH:26][CH2:27][C:28]([N:11]2[CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:8][CH2:9][CH:10]2[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:29])[CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 149969602-{[(3-Methylphenyl)carbamoyl]amino}acetic acidHCID 15374578HCID 15374578, compound

Product 1

HCID 131719903HCID 131719903, compoundYield 29.2%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

By proceeding in a fashion similar to that described in Example 1 but starting from 2.2 g of ethyl (2RS,5SR)-5-phenylprolinate, 2.1 g of 2-[3-(3-methylphenyl)ureido]acetic acid in suspension in 50 cm3 of anhydrous 1,2-dichloroethane and 0.72 cm3 of sulphinyl chloride, 1.2 g of ethyl (2RS,5SR)-1-{2-[3-(3-methylphenyl)ureido]acetyl}-5-phenylprolinate, melting at 115° C., are obtained after recrystallization in acetonitrile.

Sources & evidence

ORD record
ord-a76ea087e14c482996014311f5cb7ed4
Source dataset
uspto-grants-1997_03
Patent number
US05610144

Reaction notes

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