Sodium Hydroxide → HCID 67098011, compound

HRID 2078650Notes

Reaction equation

HRID 2078650 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][CH:47]([CH3:49])[CH3:48])=[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]([CH3:45])([CH3:44])[CH3:43])=[CH:24][CH:25]=2)=[CH:16][C:15]=1[O:46][CH:47]([CH3:49])[CH3:48])=[O:13])(=[O:10])=[O:9]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67097616HCID 67097616, compound

Product 1

HCID 67098011HCID 67098011, compoundYield 102.1%

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-isopropoxy-4-biphenylyl]carbonyl]amino]sulfonyl]propyl acetate (221 mg) in methanol (2.21 ml) and tetrahydrofuran (1.11 ml) was added 1N sodium hydroxide (0.950 ml) and the mixture was stirred at room temperature for 1 hour. Methanol and tetrahydrofuran were removed by evaporation under reduced pressure and to the residue was added water (50 ml). The mixture was acidified with 1N hydrochloric acid (pH=5.4) and extracted with ethyl acetate (50 ml×2). The combined organic layer was 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′-isopropoxy-4-biphenylyl]propyl][(2R)-2-hydroxy-2-(3-pyridyl)ethyl]carbamate (212 mg) as a white solid.

Workup

  1. customMethanol and tetrahydrofuran were removed by evaporation under reduced pressure and to the residue
  2. additionwas added water (50 ml)
  3. extractionextracted with ethyl acetate (50 ml×2)
  4. washThe combined organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationFiltration
  7. customfollowed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-724f952cd97a4c4092b55ddd555a9340
Source dataset
uspto-grants-2011_04
Patent number
US07928264B2

Reaction notes

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