HCID 86751932, compound → HCID 86751915, compound

HRID 725873Notes

Reaction equation

HRID 725873 reaction equation
C([O:8][C:9]([C:11]1[CH:12]=[C:13]([NH:17][C:18](=[O:50])[NH:19][CH2:20][C:21]([N:23]2[CH:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:26]([C:34](=[O:42])[NH:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH2:25][CH:24]2[C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])=[O:22])[CH:14]=[CH:15][CH:16]=1)=[O:10])C1C=CC=CC=1>C(O)C.[Pd]>[C:46]([O:45][C:43]([CH:24]1[CH2:25][CH:26]([C:34](=[O:42])[NH:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:23]1[C:21](=[O:22])[CH2:20][NH:19][C:18](=[O:50])[NH:17][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=1)[C:9]([OH:10])=[O:8])=[O:44])([CH3:49])([CH3:47])[CH3:48]

Participants

4

Reactant 1

HCID 86751932HCID 86751932, compound

Product 1

HCID 86751915HCID 86751915, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A The reaction is carried out in a way analogous to that described in Example 2A, but from 2.6 g of tert-butyl (2RS,4RS,5SR)-1-{2-[3-(3-(benzyloxycarbonyl)phenyl)ureido]acetyl}-5-phenyl-4-(phenylcarbamoyl)pyrrolidine-2-carboxylate and 0.3 g of 10% palladium-on-charcoal in 150 cm3 of ethanol. After treatment, there are obtained 2.05 g of (2RS,4RS,5SR)-3-{3-[2-(2-tert-butoxycarbonyl-5-phenyl-4-phenylcarbamoyl-1-pyrrolidinyl)-2-oxoethyl]ureido}benzoic acid [Rf =0.15; eluent: methylene chloride/methanol (80/20)].

Sources & evidence

ORD record
ord-025a8c7ec1c94166ba5c4ea356d8e490
Source dataset
uspto-grants-1998_01
Patent number
US05707991

Reaction notes

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