Sodium Hydroxide → HCID 67098219, compound

HRID 2078649Notes

Reaction equation

HRID 2078649 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][S:8]([NH:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][N:29]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:30][C@H:31]([OH:38])[C:32]3[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=3)=[CH:22][CH:21]=2)=[CH:16][C:15]=1[O:46][CH2:47][CH:48]([CH3:50])[CH3:49])=[O:13])(=[O:10])=[O:9])(=O)C.[OH-].[Na+]>CO.O1CCCC1>[OH:4][CH2:5][CH2:6][CH2:7][S:8]([NH:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:21]=[CH:22][C:23]([CH2:26][CH2:27][CH2:28][N:29]([CH2:30][C@H:31]([OH:38])[C:32]3[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=3)[C:39](=[O:40])[O:41][C:42]([CH3:44])([CH3:45])[CH3:43])=[CH:24][CH:25]=2)=[CH:16][C:15]=1[O:46][CH2:47][CH:48]([CH3:50])[CH3:49])=[O:13])(=[O:10])=[O:9]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67097363HCID 67097363, compound

Product 1

HCID 67098219HCID 67098219, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[[[[4′-[3-[(tert-butoxycarbonyl)-[(2R)-2-hydroxy-2-(3-pyridyl)ethyl]amino]propyl]-3-isobutoxy-4-biphenylyl]carbonyl]amino]sulfonyl]propyl acetate (108 mg) in methanol (1.08 ml) and tetrahydrofuran (0.324 ml) was added 1N aqueous sodium hydroxide solution (0.455 ml) and the mixture was stirred at room temperature for 45 minutes. The reaction mixture was concentrated under reduced pressure and the pH value was adjusted to 6.0 with 0.1N hydrochloric acid. The mixture was extracted with ethyl acetate (twice) and the extracts were washed with water and brine, and dried over magnesium sulfate. Filtration followed by evaporation under reduced pressure gave tert-butyl [3-[4′-[[[(3-hydroxypropyl)sulfonyl]amino]carbonyl]-3′-isobutoxy-4-biphenylyl]-propyl][(2R)-2-hydroxy-2-(3-pyridyl)ethyl]carbamate (91.1 mg) as a white solid (foam).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionThe mixture was extracted with ethyl acetate (twice) and the extracts
  3. washwere washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationFiltration
  6. customfollowed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-bcf9936d1a6c4048b46184b5a0fa8496
Source dataset
uspto-grants-2011_04
Patent number
US07928264B2

Reaction notes

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