Methanol → HCID 67097916, compound

HRID 2078642Notes

Reaction equation

HRID 2078642 reaction equation
C([O:8][CH2:9][CH2:10][S:11]([NH:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][N:31]([CH2:39][C@H:40]([OH:50])[C:41]3[CH:46]=[CH:45][C:44]([N+:47]([O-])=O)=[CH:43][CH:42]=3)[C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:25][CH:24]=2)=[CH:19][C:18]=1[O:51][CH:52]1[CH2:57][CH2:56][CH2:55][CH2:54][CH2:53]1)=[O:16])(=[O:13])=[O:12])C1C=CC=CC=1.C([O-])=O.[NH4+].CO>[Pd].O>[NH2:47][C:44]1[CH:45]=[CH:46][C:41]([C@@H:40]([OH:50])[CH2:39][N:31]([CH2:30][CH2:29][C:26]2[CH:27]=[CH:28][C:23]([C:20]3[CH:21]=[CH:22][C:17]([C:15]([NH:14][S:11]([CH2:10][CH2:9][OH:8])(=[O:13])=[O:12])=[O:16])=[C:18]([O:51][CH:52]4[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57]4)[CH:19]=3)=[CH:24][CH:25]=2)[C:32](=[O:38])[O:33][C:34]([CH3:35])([CH3:37])[CH3:36])=[CH:42][CH:43]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 2723923Ammonium formateHCID 67097762HCID 67097762, compound

Product 1

HCID 67097916HCID 67097916, compoundYield 67.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of tert-butyl [2-[4′-[[[[2-(benzyloxy)-ethyl]sulfonyl]amino]carbonyl]-3′-(cyclohexyloxy)-4-biphenylyl]ethyl][(2R)-2-hydroxy-2-(4-nitrophenyl)ethyl]-carbamate (215 mg), 10% palladium on activated carbon (50% wet, 645 mg), ammonium formate (845 mg), methanol (6.45 ml) and water (0.65 ml) was refluxed for 20 minutes. After cooling to room temperature, the catalyst was removed by filtration and washed with methanol. The filtrate was concentrated in vacuo and the residue was chromatographed on silica gel (eluent: hexane/ethyl acetate) to give tert-butyl [(2R)-2-(4-aminophenyl)-2-hydroxyethyl][2-[3′-(cyclohexyloxy)-4′-[[[(2-hydroxyethyl)sulfonyl]amino]carbonyl]-4-biphenylyl]ethyl]-carbamate (123 mg) as a pale-yellow solid.

Workup

  1. temperaturewas refluxed for 20 minutes
  2. customthe catalyst was removed by filtration
  3. washwashed with methanol
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was chromatographed on silica gel (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5d9f03302311487f8700978de4000f54
Source dataset
uspto-grants-2011_04
Patent number
US07928264B2

Reaction notes

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