HCID 86751920, compound → HCID 19709599, compound

HRID 725866Notes

Reaction equation

HRID 725866 reaction equation
[C:1]([O:5][C:6]([CH:8]1[CH2:12][CH:11]([S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH:10]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[F:28])[N:9]1[C:29](=[O:52])[CH2:30][NH:31][C:32](=[O:51])[NH:33][C:34]1[CH:35]=[C:36]([CH2:40][C:41]([O:43]CC2C=CC=CC=2)=[O:42])[CH:37]=[CH:38][CH:39]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([CH:8]1[CH2:12][CH:11]([S:13]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)(=[O:14])=[O:15])[CH:10]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[F:28])[N:9]1[C:29](=[O:52])[CH2:30][NH:31][C:32](=[O:51])[NH:33][C:34]1[CH:35]=[C:36]([CH2:40][C:41]([OH:43])=[O:42])[CH:37]=[CH:38][CH:39]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 86751920HCID 86751920, compound

Product 1

HCID 19709599HCID 19709599, compoundYield 46%

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 3.6 g of benzyl (2RS,4SR,5RS)-3-{3-[2-(2-tert-butoxycarbonyl-5-(2-fluorophenyl)-4-phenylsulphonyl-1-pyrrolidinyl)-2-oxoethyl]ureido}phenylacetate 0.4 g of 10% palladium-on-charcoal in 200 cm3 of ethanol. After treatment, there are obtained 1.45 g of (2RS,4SR,5RS)-3-{3-[2-(2-tert-butoxycarbonyl-5-(2-fluorophenyl)-4-phenylsulphonyl-1-pyrrolidinyl)-2-oxoethyl]ureido}phenylacetic acid [Rf =0.27; eluent: methylene chloride/methanol (80/20)].

Sources & evidence

ORD record
ord-c01af9693b4643258fcb1f8575cc5b87
Source dataset
uspto-grants-1998_01
Patent number
US05707991

Reaction notes

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