2-{[(3-Methylphenyl)carbamoyl]amino}acetic acid → HCID 131719904, compound

HRID 975951Notes

Reaction equation

HRID 975951 reaction equation
[C:1]1([CH:7]2[NH:11][CH:10]([C:12](OCC3CC3)=[O:13])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:19][C:20]1[CH:21]=[C:22]([NH:26][C:27](=[O:33])[NH:28][CH2:29][C:30]([OH:32])=[O:31])[CH:23]=[CH:24][CH:25]=1>ClCCCl.S(Cl)(Cl)=O>[CH3:19][C:20]1[CH:21]=[C:22]([NH:26][C:27](=[O:33])[NH:28][CH2:29][C:30]([O:32][C:12](=[O:13])[C@@H:10]2[CH2:9][CH2:8][CH:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[NH:11]2)=[O:31])[CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 149969602-{[(3-Methylphenyl)carbamoyl]amino}acetic acidHCID 131719905HCID 131719905, compound

Product 1

HCID 131719904HCID 131719904, compound

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 g of cyclopropyl-methyl (2RS,5SR)-5-phenylprolinate, 1.7 g of 2-[3-(3-methylphenyl)ureido]acetic acid in suspension in 50 cm3 of anhydrous 1,2-dichloroethane and 0.6 cm3 of sulphinyl chloride, 1.1 g of cyclopropylmethyl (2RS,5SR)-1-{2-[3-(3-methylphenyl)ureido}acetyl-5-phenylprolinate, melting at 130° C., are obtained after recrystallization in acetonitrile.

Sources & evidence

ORD record
ord-dbbde238d4b649568f15be3483c1cec7
Source dataset
uspto-grants-1997_03
Patent number
US05610144

Reaction notes

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