Lithium hydroxide, monohydrate → 4-((tert-butoxycarbonylamino)methyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylic acid

HRID 423031Notes

Reaction equation

HRID 423031 reaction equation
O.[OH-].[Li+].[C:4]([O:8][C:9]([NH:11][CH2:12][C:13]1([C:28]([O:30]CC)=[O:29])[CH2:18][CH2:17][N:16]([C:19]2[C:20]3[CH:27]=[CH:26][NH:25][C:21]=3[N:22]=[CH:23][N:24]=2)[CH2:15][CH2:14]1)=[O:10])([CH3:7])([CH3:6])[CH3:5]>O.C1COCC1.C(O)C.CCOC(C)=O>[C:4]([O:8][C:9]([NH:11][CH2:12][C:13]1([C:28]([OH:30])=[O:29])[CH2:14][CH2:15][N:16]([C:19]2[C:20]3[CH:27]=[CH:26][NH:25][C:21]=3[N:22]=[CH:23][N:24]=2)[CH2:17][CH2:18]1)=[O:10])([CH3:7])([CH3:5])[CH3:6]

Participants

7

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 57750296ethyl 4-((tert-butoxycarbonylamino)methyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylate2×

Product 1

HCID 446042214-((tert-butoxycarbonylamino)methyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylic acidYield 63.1%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

Lithium hydroxide monohydrate (0.556 g, 13.26 mmol) was added to ethyl 4-((tert-butoxycarbonylamino)methyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylate (Intermediate 11) (1.07 g, 2.65 mmol) in water (6.25 ml), THF (25 ml) and ethanol (25.00 ml). The resulting solution was stirred at 20° C. for 1 day. The reaction mixture was diluted with EtOAc (20 mL) and washed with water (20 mL). The aqueous was adjusted to pH5 with 1M citric acid solution then extracted with EtOAc (3×50 mL). The organic extracts were washed with saturated brine (25 mL) then dried over MgSO4, filtered and evaporated to afford desired product 4-((tert-butoxycarbonylamino)methyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylic acid (0.628 g, 63.1%) as a white foam.

Workup

  1. washwashed with water (20 mL)
  2. extractionthen extracted with EtOAc (3×50 mL)
  3. washThe organic extracts were washed with saturated brine (25 mL)
  4. dry with materialthen dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-61da7afaeaaf4b2d9eafb3e4eca40de7
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

Loading…