Ethyl Acetate → HCID 19102823, compound

HRID 1198700Notes

Reaction equation

HRID 1198700 reaction equation
[C:1]([O:5][C:6]([NH:8][S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[CH:23]=[CH:22][C:21]([CH2:24][N:25]2[C:29]([CH2:30][CH2:31][CH2:32][CH3:33])=[N:28][N:27]([C:34]3[CH:39]=[C:38]([N+:40]([O-])=O)[CH:37]=[CH:36][C:35]=3[C:43]([F:46])([F:45])[F:44])[C:26]2=[O:47])=[C:20]([F:48])[CH:19]=1)(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OCC)(=O)C.[H][H]>[Pt]=O.C(O)C>[NH2:40][C:38]1[CH:37]=[CH:36][C:35]([C:43]([F:44])([F:45])[F:46])=[C:34]([N:27]2[C:26](=[O:47])[N:25]([CH2:24][C:21]3[CH:22]=[CH:23][C:18]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=4[S:9](=[O:10])(=[O:11])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[CH:19][C:20]=3[F:48])[C:29]([CH2:30][CH2:31][CH2:32][CH3:33])=[N:28]2)[CH:39]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 19102799HCID 19102799, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19102823HCID 19102823, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A mixture of 185 mg (0.267 mmol) of 4-[[2'-[N-(t-butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-2-[5-nitro-2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one (from Step C), 25 mg of platinum oxide, 2 mL of ethyl acetate, and 10 mL of ethanol was shaken with hydrogen at approximately 3 atm for 2 hours. The mixture was centrifuged, and the supernatant was concentrated. Flash chromatography of the residue on silica gel (gradient elution with 1-5% MeOH in CH2Cl2) yielded 118 mg (67%) of the title compound as a white foam, homogeneous by TLC (95:5 CH2Cl2 --MeOH); mass spectrum (FAB) m/e 664 (M+1)+.

Workup

  1. concentrationthe supernatant was concentrated

Sources & evidence

ORD record
ord-299954e03e6e4f32bcb41a14f07c3175
Source dataset
uspto-grants-1994_01
Patent number
US05281614

Reaction notes

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