Sodium Hydroxide → (3R,5S)-1-(tert-butoxycarbonyl)-5-[({2-tert-butyl-4-[(1,3-oxazol-2-ylmethyl)amino]pyrimidin-5-yl}carbonyl)(2-methylpropyl)amino]piperidine-3-carboxylic acid

HRID 2192797Notes

Reaction equation

HRID 2192797 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([NH:11][CH2:12][C:13]2[O:14][CH:15]=[CH:16][N:17]=2)[C:8]([C:18]([N:20]([CH2:38][CH:39]([CH3:41])[CH3:40])[C@@H:21]2[CH2:26][N:25]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:24][C@H:23]([C:34]([O:36]C)=[O:35])[CH2:22]2)=[O:19])=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:30]([O:29][C:27]([N:25]1[CH2:26][C@@H:21]([N:20]([C:18]([C:8]2[C:9]([NH:11][CH2:12][C:13]3[O:14][CH:15]=[CH:16][N:17]=3)=[N:10][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[N:6][CH:7]=2)=[O:19])[CH2:38][CH:39]([CH3:41])[CH3:40])[CH2:22][C@@H:23]([C:34]([OH:36])=[O:35])[CH2:24]1)=[O:28])([CH3:32])([CH3:33])[CH3:31]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 596253251-tert-Butyl 3-methyl (3R,5S)-5-[({2-tert-butyl-4-[(1,3-oxazol-2-ylmethyl)amino]pyrimidin-5-yl}carbonyl) (2-methylpropyl)amino]piperidine-1,3-dicarboxylate

Product 1

HCID 59625191(3R,5S)-1-(tert-butoxycarbonyl)-5-[({2-tert-butyl-4-[(1,3-oxazol-2-ylmethyl)amino]pyrimidin-5-yl}carbonyl)(2-methylpropyl)amino]piperidine-3-carboxylic acidYield 98.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-tert-Butyl 3-methyl (3R,5S)-5-[({2-tert-butyl-4-[(1,3-oxazol-2-ylmethyl)amino]pyrimidin-5-yl}carbonyl) (2-methylpropyl)amino]piperidine-1,3-dicarboxylate (0.26 g) was dissolved in methanol (3 ml), 2 M aqueous sodium hydroxide solution (1.0 ml) was added and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, the residue was diluted with saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the object compound (0.25 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with saturated aqueous ammonium chloride solution
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-09973272bd78451793887325a6229684
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

Loading…