Sodium Hydroxide → HCID 59625183, compound

HRID 2192824Notes

Reaction equation

HRID 2192824 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([NH:11][CH2:12][CH2:13][CH2:14][S:15][CH3:16])[C:8]([C:17]([N:19]([CH2:42][CH:43]([CH3:45])[CH3:44])[C@H:20]2[CH2:25][C@@H:24]([NH:26][C:27]([O:29][CH2:30][C:31](Cl)(Cl)Cl)=[O:28])[CH2:23][N:22]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:21]2)=[O:18])=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C.O>[C:1]([C:5]1[N:10]=[C:9]([NH:11][CH2:12][CH2:13][CH2:14][S:15][CH3:16])[C:8]([C:17]([N:19]([CH2:42][CH:43]([CH3:44])[CH3:45])[C@H:20]2[CH2:25][C@@H:24]([NH:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:23][N:22]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:21]2)=[O:18])=[CH:7][N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59625576HCID 59625576, compound

Product 1

HCID 59625183HCID 59625183, compoundYield 12.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of tert-butyl (3S,5R)-3-{[(2-tert-butyl-4-{[3-(methylsulfanyl)propyl]amino}pyrimidin-5-yl)carbonyl](2-methylpropyl)amino}-5-{[(2,2,2-trichloroethoxy)carbonyl]amino}piperidine-1-carboxylate (1.12 g) in ethanol (10 ml) was added 4 M aqueous sodium hydroxide solution (10 ml), and the mixture was stirred at 80° C. for 12 hr. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, eluted with ethyl acetate-hexane (10:90-85:15) and concentrated under reduced pressure to give the object compound (119 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washeluted with ethyl acetate-hexane (10:90-85:15)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2c9d8846e0b64f6e9b0e136ffcc87f1c
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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