Ethyl Acetate → HCID 69537388, compound

HRID 2220426Notes

Reaction equation

HRID 2220426 reaction equation
[CH:1]1([O:7][C:8]2[CH:9]=[C:10]([C:21]3[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][N:30]([CH2:38][C@H:39]([OH:49])[C:40]4[CH:45]=[CH:44][C:43]([N+:46]([O-])=O)=[CH:42][CH:41]=4)[C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:23][CH:22]=3)[CH:11]=[CH:12][C:13]=2[C:14]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[O:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl-].[NH4+].C(OCC)(=O)C>O.C(O)C.[Fe]>[NH2:46][C:43]1[CH:42]=[CH:41][C:40]([C@@H:39]([OH:49])[CH2:38][N:30]([CH2:29][CH2:28][CH2:27][C:24]2[CH:25]=[CH:26][C:21]([C:10]3[CH:11]=[CH:12][C:13]([C:14]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[O:15])=[C:8]([O:7][CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)[CH:9]=3)=[CH:22][CH:23]=2)[C:31](=[O:37])[O:32][C:33]([CH3:34])([CH3:36])[CH3:35])=[CH:45][CH:44]=1

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 86760724HCID 86760724, compound

Product 1

HCID 69537388HCID 69537388, compoundYield 67.4%

Reagents, catalysts & solvents 3

HCID 23925IronCatalyst2×HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of tert-butyl [3-[3′-(cyclohexyloxy)-4′-[[(methylsulfonyl)amino]carbonyl]-4-biphenylyl]propyl][(2R)-2-hydroxy-2-(4-nitrophenyl)ethyl]carbamate (200 mg), iron powder (48.2 mg) and ammonium chloride (7.7 mg) in water (1.0 ml) and ethanol (3.0 ml) was stirred 80° C. for 1 hour. After cooling to room temperature, ethyl acetate (15 ml) was added to the reaction mixture and iron powder was removed by filtration through a Celite cake. The filtrate was washed with water and brine and dried over magnesium sulfate. Filtration followed by evaporation under reduced pressure gave a crude product which was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=1/1) to give tert-butyl [(2R)-2-(4-aminophenyl)-2-hydroxyethyl][3-[3′-[cyclohexyloxy]-4′-[[(methylsulfonyl)-amino]carbonyl]-4-biphenylyl]propyl]carbamate (129 mg) as a white solid (foam).

Workup

  1. temperatureAfter cooling to room temperature
  2. customwas removed by filtration through a Celite cake
  3. washThe filtrate was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationFiltration
  6. customfollowed by evaporation under reduced pressure
  7. customgave a crude product which
  8. customwas purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-ab05fa37e7a34481b48872de0ff5ab8c
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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