Ammonium formate → HCID 67097248, compound

HRID 2078667Notes

Reaction equation

HRID 2078667 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C@@H:8]([OH:49])[CH2:9][N:10]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([C:32]([NH:34][S:35]([CH2:38][CH2:39][CH2:40][OH:41])(=[O:37])=[O:36])=[O:33])=[C:28]([O:42][CH:43]4[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]4)[CH:27]=3)=[CH:22][CH:21]=2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:4][CH:3]=1.C([O-])=O.[NH4+]>[Pd].CO.O>[CH:43]1([O:42][C:28]2[CH:27]=[C:26]([C:23]3[CH:24]=[CH:25][C:20]([CH2:19][CH2:18][N:10]([CH2:9][C@H:8]([OH:49])[C:5]4[CH:6]=[N:7][CH:2]=[CH:3][CH:4]=4)[C:11](=[O:17])[O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[CH:21][CH:22]=3)[CH:31]=[CH:30][C:29]=2[C:32]([NH:34][S:35]([CH2:38][CH2:39][CH2:40][OH:41])(=[O:36])=[O:37])=[O:33])[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 86618362HCID 86618362, compound

Product 1

HCID 67097248HCID 67097248, compoundYield 84.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The mixture of tert-butyl [(2R)-2-(6-chloro-3-pyridyl)-2-hydroxyethyl][2-[3′-(cyclohexyloxy)-4′-[[[(3-hydroxypropyl)sulfonyl]amino]carbonyl]-4-biphenylyl]-ethyl]carbamate (145 mg), ammonium formate (128 mg) and palladium on carbon powder (50 mg) in methanol (2 ml) and water (0.2 ml) was refluxed for 50 minutes. The catalyst was filtered off and the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (chloroform/methanol=94/6) to give tert-butyl [2-[3′-(cyclohexyloxy)-4′-[[[(3-hydroxypropyl)sulfonyl]amino]carbonyl]-4-biphenylyl]ethyl][(2R)-2-hydroxy-2-(3-pyridyl)ethyl]carbamate (117 mg).

Workup

  1. temperaturewas refluxed for 50 minutes
  2. filtrationThe catalyst was filtered off
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (chloroform/methanol=94/6)

Sources & evidence

ORD record
ord-99239b19d08e41a988da2d350553f3bd
Source dataset
uspto-grants-2011_04
Patent number
US07928264B2

Reaction notes

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