HCID 4026994, compound → HCID 14880518, compound

HRID 1588852Notes

Reaction equation

HRID 1588852 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:22])[NH:10][CH:11]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12]([OH:14])=O)[CH:5]=[CH:6][CH:7]=1.[NH:23]([CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>ClCCCl.S(Cl)(Cl)=O>[CH3:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:22])[NH:10][CH:11]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12]([N:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:35])[CH3:36])=[O:32])=[O:14])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 4026994HCID 4026994, compoundHCID 12433731HCID 12433731, compound

Product 1

HCID 14880518HCID 14880518, compoundYield 41.2%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

Working as in Example 15, but starting with (RS)-2-[3-(3-methylphenyl)ureido]-3-phenylpropanoic acid (4.8 g) and tert-butyl anilinoacetate (3.3 g) in anhydrous 1,2-dichloroethane (300 cc) and thionyl chloride (1.16 cc), and recrystallizing successively in diethyl ether and then in isopropanol, tert-butyl (RS)-N-{2-[3-(3-methylphenyl)ureido]-3-phenylpropionyl}-N-phenylglycinate (3.2 g), m.p. 198° C., is obtained.

Workup

  1. customrecrystallizing successively in diethyl ether

Sources & evidence

ORD record
ord-39d4dd4c81f14e9e8bec834cedaacf2c
Source dataset
uspto-grants-1993_06
Patent number
US05223529

Reaction notes

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