Lithium hydroxide, monohydrate → Lithium 2-(2-(2-(2-((4-(1-(tert-butoxycarbonyl)piperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)propanoate

HRID 1485185Notes

Reaction equation

HRID 1485185 reaction equation
O[Li:2].O.C[O:5][C:6](=[O:47])[CH:7]([C:9]1[CH:46]=[CH:45][CH:44]=[CH:43][C:10]=1[CH2:11][CH2:12][C:13]1[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][N:16]=[C:15]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([CH:30]3[CH2:35][CH2:34][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:32][CH2:31]3)=[CH:26][CH:25]=2)[N:14]=1)[CH3:8]>C1COCC1.O.CO>[C:39]([O:38][C:36]([N:33]1[CH2:34][CH2:35][CH:30]([C:27]2[CH:26]=[CH:25][C:24]([NH:23][C:15]3[N:14]=[C:13]([CH2:12][CH2:11][C:10]4[CH:43]=[CH:44][CH:45]=[CH:46][C:9]=4[CH:7]([CH3:8])[C:6]([O-:47])=[O:5])[C:18]([C:19]([F:21])([F:20])[F:22])=[CH:17][N:16]=3)=[CH:29][CH:28]=2)[CH2:31][CH2:32]1)=[O:37])([CH3:40])([CH3:41])[CH3:42].[Li+:2]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 71209279Tert-butyl 4-(4-((4-(2-(1-methoxy-1-oxopropan-2-yl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate

Product 1

HCID 71208836Lithium 2-(2-(2-(2-((4-(1-(tert-butoxycarbonyl)piperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)propanoate

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiOH.H2O (17.3 mg, 0.413 mmol) was added to a solution of tert-butyl 4-(4-((4-(2-(1-methoxy-1-oxopropan-2-yl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate (I53) (0.084 g, 0.137 mmol) in THF (7 mL), water (1.5 mL) and methanol (1 mL). The resulting mixture was allowed to stir at room temperature for 20 hours. The volatiles were removed in vacuo and the residue diluted with EtOAc (50 mL) and sat. aq. NaHCO3 (50 mL). The layers were separated and the aqueous layer was extracted with EtOAc (1×50 mL). The organic layers were combined, washed with brine (50 mL), dried with Na2SO4, filtered and concentrated under reduced pressure to give the title compound (I54) (86 mg) as a pale yellow viscous oil.

Workup

  1. customThe volatiles were removed in vacuo
  2. additionthe residue diluted with EtOAc (50 mL) and sat. aq. NaHCO3 (50 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc (1×50 mL)
  5. washwashed with brine (50 mL)
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-73c063bd79e74c14a2af2e9d405edf7d
Source dataset
uspto-grants-2016_08
Patent number
US09421205B2

Reaction notes

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