Sodium Hydroxide → 4-(tert-butoxycarbonylamino)-1-(5-cyclopropyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylic acid

HRID 423081Notes

Reaction equation

HRID 423081 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([NH:10][C:11]1([C:39]([O:41]C)=[O:40])[CH2:16][CH2:15][N:14]([C:17]2[C:18]3[C:25]([CH:26]4[CH2:28][CH2:27]4)=[CH:24][N:23](S(C4C=CC(C)=CC=4)(=O)=O)[C:19]=3[N:20]=[CH:21][N:22]=2)[CH2:13][CH2:12]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>C1COCC1.CCOC(C)=O>[C:3]([O:7][C:8]([NH:10][C:11]1([C:39]([OH:41])=[O:40])[CH2:12][CH2:13][N:14]([C:17]2[C:18]3[C:25]([CH:26]4[CH2:27][CH2:28]4)=[CH:24][NH:23][C:19]=3[N:20]=[CH:21][N:22]=2)[CH2:15][CH2:16]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57750287methyl 4-(tert-butoxycarbonylamino)-1-(5-cyclopropyl-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylate2×

Product 1

HCID 577503464-(tert-butoxycarbonylamino)-1-(5-cyclopropyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylic acidYield 68.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

2M sodium hydroxide solution (5.00 mL) was added to methyl 4-(tert-butoxycarbonylamino)-1-(5-cyclopropyl-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylate (Intermediate 63) (780 mg, 1.37 mmol) in THF (10 mL) at 20° C. The resulting solution was stirred at 40° C. for 24 hours. The reaction mixture was diluted with EtOAc (50 mL) and the aqueous layer was collected and acidified to pH4 with 2M HCl solution. The aqueous layer was extracted with DCM (2×50 mL) and the organic layers combined and washed with saturated brine (50 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product 4-(tert-butoxycarbonylamino)-1-(5-cyclopropyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylic acid (375 mg, 68.2%) as a cream solid.

Workup

  1. customthe aqueous layer was collected
  2. extractionThe aqueous layer was extracted with DCM (2×50 mL)
  3. washwashed with saturated brine (50 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-a11ccb64ed894fcd90c8962c38b2578b
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

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