HCID 19709489, compound → HCID 19709473, compound

HRID 725876Notes

Reaction equation

HRID 725876 reaction equation
C([O:8][C:9]([CH2:11][C:12]1[CH:13]=[C:14]([NH:18][C:19](=[O:57])[NH:20][CH2:21][C:22]([N:24]2[CH:28]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[F:35])[CH:27]([S:36]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)(=[O:38])=[O:37])[CH2:26][CH:25]2[C:45]([N:47]2[C:56]3[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=3)[CH2:50][CH2:49][CH2:48]2)=[O:46])=[O:23])[CH:15]=[CH:16][CH:17]=1)=[O:10])C1C=CC=CC=1>C(O)C.[Pd]>[F:35][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[CH:28]1[N:24]([C:22](=[O:23])[CH2:21][NH:20][C:19](=[O:57])[NH:18][C:14]2[CH:13]=[C:12]([CH2:11][C:9]([OH:10])=[O:8])[CH:17]=[CH:16][CH:15]=2)[CH:25]([C:45]([N:47]2[C:56]3[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=3)[CH2:50][CH2:49][CH2:48]2)=[O:46])[CH2:26][CH:27]1[S:36]([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)(=[O:37])=[O:38]

Participants

4

Reactant 1

HCID 19709489HCID 19709489, compound

Product 1

HCID 19709473HCID 19709473, compoundYield 66.6%

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 2.83 g of (2RS,4SR,5RS)-1-{2-[3-(3-(benzyloxycarbonylmethyl)phenyl)ureido]acetyl}-5-(2-fluorophenyl)-2-(1,2,3,4-tetrahydro-1-quinolylcarbonyl)-4-(phenylsulphonyl)pyrrolidine and 0.36 g of 10% palladium-on-charcoal in 150 cm3 of ethanol. After treatment, there are obtained 1.67 g of (2RS,4RS,5SR)-3-{3-[2-(5-(2-fluorophenyl)-2-(1,2,3,4-tetrahydro-1-quinolylcarbonyl)-4-(phenylsulphonyl)-1-pyrrolidinyl)-2-oxoethyl]ureido}phenylacetic acid [Rf =0.49; eluent: methylene chloride/methanol (90/10)].

Sources & evidence

ORD record
ord-7b604935ff5e449b8667dbb48898e45d
Source dataset
uspto-grants-1998_01
Patent number
US05707991

Reaction notes

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