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

HRID 2192780Notes

Reaction equation

HRID 2192780 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([NH:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])[C:8]([C:17]([N:19]([CH2:37][CH:38]([CH3:40])[CH3:39])[C@@H:20]2[CH2:25][N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:23][C@H:22]([C:33]([O:35]C)=[O:34])[CH2:21]2)=[O:18])=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO.C1COCC1>[C:29]([O:28][C:26]([N:24]1[CH2:25][C@@H:20]([N:19]([C:17]([C:8]2[C:9]([NH:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])=[N:10][C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[N:6][CH:7]=2)=[O:18])[CH2:37][CH:38]([CH3:40])[CH3:39])[CH2:21][C@@H:22]([C:33]([OH:35])=[O:34])[CH2:23]1)=[O:27])([CH3:30])([CH3:32])[CH3:31]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 596254311-tert-Butyl 3-methyl (3R,5S)-5-[({2-tert-butyl-4-[(3-methoxypropyl)amino]pyrimidin-5-yl}carbonyl)(isobutyl)amino]piperidine-1,3-dicarboxylate

Product 1

HCID 59625174(3R*,5S*)-1-(tert-butoxycarbonyl)-5-[({2-tert-butyl-4-[(3-methoxypropyl)amino]pyrimidin-5-yl}carbonyl)(2-methylpropyl)amino]piperidine-3-carboxylic acidYield 99.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-tert-Butyl 3-methyl (3R,5S)-5-[({2-tert-butyl-4-[(3-methoxypropyl)amino]pyrimidin-5-yl}carbonyl)(isobutyl)amino]piperidine-1,3-dicarboxylate (1.08 g) was dissolved in methanol (25 ml) and THF (12 ml), 2 M aqueous sodium hydroxide solution (4.79 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 magnesium sulfate, and concentrated under reduced pressure to give the object compound (1.05 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 magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5fb9499bb5b34c4a8f5cfdedf9c7923e
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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