HCID 18928063, compound → tert-butyl (2RS,5RS)-1-{2-[3-(3-benzyloxycarbonylphenyl)ureido]-acetyl}-5-phenylprolinate

HRID 976001Notes

Reaction equation

HRID 976001 reaction equation
[NH2:1][CH2:2][C:3]([N:5]1[CH:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:15][CH2:14][CH:6]1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[O:4].[N:23]([C:26]1[CH:27]=[C:28]([CH:39]=[CH:40][CH:41]=1)[C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])=[C:24]=[O:25]>O1CCCC1>[CH2:32]([O:31][C:29]([C:28]1[CH:27]=[C:26]([NH:23][C:24](=[O:25])[NH:1][CH2:2][C:3]([N:5]2[CH:16]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:15][CH2:14][CH:6]2[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[O:4])[CH:41]=[CH:40][CH:39]=1)=[O:30])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 18928063HCID 18928063, compoundHCID 19700417Benzyl 3-isocyanatobenzoate

Product 1

HCID 76139539tert-butyl (2RS,5RS)-1-{2-[3-(3-benzyloxycarbonylphenyl)ureido]-acetyl}-5-phenylprolinateYield 28.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The operation is carried out in a fashion similar to that described in Example 2, but starting from 1.93 g of tert-butyl (2RS,5SR)-1-(2-aminoacetyl)-5-phenylprolinate and 3.61 g of benzyl 3-isocyanatobenzoate in 50 cm3 of tetrahydrofuran. After treatment, 1 g of tert-butyl (2RS,5SR)-1-{2-[3-(3-benzyloxycarbonylphenyl)-ureido]acetyl)-5-phenylprolinate, melting at 75° C., is obtained.

Sources & evidence

ORD record
ord-1af4f31199c64f3bbbb8724b9e869da9
Source dataset
uspto-grants-1997_03
Patent number
US05610144

Reaction notes

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