Ethanol → HCID 19700421, compound

HRID 861863Notes

Reaction equation

HRID 861863 reaction equation
C([O:8][C:9]([C:11]1[CH:12]=[C:13]([NH:17][C:18](=[O:53])[NH:19][CH2:20][C:21]([N:23]2[CH:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[F:34])[CH:26]([S:35]([N:38]3[CH2:43][CH2:42][O:41][CH2:40][CH2:39]3)(=[O:37])=[O:36])[CH2:25][CH:24]2[C:44](=[O:52])[NH:45][CH2:46][CH2:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:22])[CH:14]=[CH:15][CH:16]=1)=[O:10])C1C=CC=CC=1.C(O)C>[Pd].C(Cl)Cl.CO>[CH3:49][C:48]([CH3:51])([CH3:50])[CH2:47][CH2:46][NH:45][C:44]([CH:24]1[CH2:25][CH:26]([S:35]([N:38]2[CH2:39][CH2:40][O:41][CH2:42][CH2:43]2)(=[O:37])=[O:36])[CH:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[F:34])[N:23]1[C:21](=[O:22])[CH2:20][NH:19][C:18](=[O:53])[NH:17][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=1)[C:9]([OH:10])=[O:8])=[O:52]

Participants

5

Reactant 2

HCID 702EthanolHCID 19700393HCID 19700393, compound

Product 1

HCID 19700421HCID 19700421, compoundYield 83.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

A The process is performed as described in Example 2A, but starting with 3 g of (2RS,4SR,5RS)-1-{2-[3-(3-benzyloxycarbonylphenyl)ureido]acetyl}-5-(2-fluorophenyl)-4-morpholinosulphonyl-2-(3,3-dimethylbutyl)carbamoylpyrrolidine, 0.3 g of 10% palladium-on-charcoal and 100 cm3 of ethanol under a hydrogen atmosphere (130 kPa). After treatment, 2.2 g of (2RS,4SR,5RS)-3-(3-{2-[2-(3,3-dimethylbutyl)carbamoyl-5-(2-fluorophenyl)-4-morpholinosulphonyl-1-pyrrolidinyl]-2-oxoethyl}ureido)benzoic acid are obtained [Rf=0.25; eluent: methylene chloride/methanol (90/10)].

Sources & evidence

ORD record
ord-2dfc2f396f6c4af78f624c707fc1bd39
Source dataset
uspto-grants-1998_02
Patent number
US05716936

Reaction notes

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