HCID 86751904, compound → HCID 9808979, compound

HRID 725857Notes

Reaction equation

HRID 725857 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]([S:34]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)(=[O:36])=[O:35])[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]([S:34]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)(=[O:35])=[O:36])[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 86751904HCID 86751904, compound

Product 1

HCID 9808979HCID 9808979, compoundYield 66.5%

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 1.9 g of tert-butyl (2RS,4RS,5RS)-1-{2-[3-(3-(benzyloxycarbonyl)phenyl)ureido]acetyl}-5-phenyl-4-(phenylsulphonyl)pyrrolidine-2-carboxylate and 0.2 g of 10% palladium-on-charcoal in 75 cm3 of ethanol. After treatment, there are obtained 1.1 g of (2RS,4RS,5RS)-3-{3-[2-(2-tert-butoxycarbonyl-5-phenyl-4-phenylsulphonyl-1-pyrrolidinyl)-2-oxoethyl]ureido}benzoic acid [Rf =0.22; eluent: methylene chloride/methanol (80/20)].

Sources & evidence

ORD record
ord-5559bbded59d4577905ccd26ed881a0c
Source dataset
uspto-grants-1998_01
Patent number
US05707991

Reaction notes

Loading…