Sodium Hydroxide → HCID 59625450, compound

HRID 2192858Notes

Reaction equation

HRID 2192858 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C@@H:10]([C:35]([O:37]C)=[O:36])[N:11]([C:16]([C:18]1[C:19]([NH:28][CH2:29][C:30]2[O:31][CH:32]=[CH:33][CH:34]=2)=[N:20][C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])=[N:22][CH:23]=1)=[O:17])[CH2:12][CH:13]([CH3:15])[CH3:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>O1CCCC1CO>[C:1]([O:5][C:6]([NH:8][CH2:9][C@@H:10]([C:35]([OH:37])=[O:36])[N:11]([C:16]([C:18]1[C:19]([NH:28][CH2:29][C:30]2[O:31][CH:32]=[CH:33][CH:34]=2)=[N:20][C:21]([C:24]([CH3:26])([CH3:27])[CH3:25])=[N:22][CH:23]=1)=[O:17])[CH2:12][CH:13]([CH3:14])[CH3:15])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59625589HCID 59625589, compound

Product 1

HCID 59625450HCID 59625450, compoundYield 123.3%

Reagents, catalysts & solvents 1

HCID 7360Tetrahydrofurfuryl alcoholSolvent

Procedure

Methyl 3-[(tert-butoxycarbonyl)amino]-N-({2-tert-butyl-4-[(furan-2-ylmethyl)amino]pyrimidin-5-yl}carbonyl)-N-(2-methylpropyl)-L-alaninate (200 mg) was dissolved in tetrahydrofuran-methanol (1:2, 18 ml), 2 M aqueous sodium hydroxide solution (0.95 ml) was added and the mixture was stirred for 4 hr. The reaction mixture was concentrated under reduced pressure, and diluted with saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and solvent was evaporated under reduced pressure to give the object compound (240 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with saturated aqueous ammonium chloride solution
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate, and solvent
  5. customwas evaporated under reduced pressure

Sources & evidence

ORD record
ord-e501b2c60b924d79b9a1128f5dade02f
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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