Lithium hydroxide, monohydrate → HCID 68282864, compound

HRID 1473160Notes

Reaction equation

HRID 1473160 reaction equation
O[Li:2].O.C[O:5][C:6](=[O:45])[CH2:7][C:8]1[CH:44]=[CH:43][CH:42]=[CH:41][C:9]=1[CH2:10][CH2:11][C:12]1[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][N:15]=[C:14]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([CH:29]3[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30]3)=[CH:25][CH:24]=2)[N:13]=1>C1COCC1.O.CO>[C:37]([O:36][C:34]([N:31]1[CH2:32][CH2:33][CH:29]([C:26]2[CH:25]=[CH:24][C:23]([NH:22][C:14]3[N:13]=[C:12]([CH2:11][CH2:10][C:9]4[CH:41]=[CH:42][CH:43]=[CH:44][C:8]=4[CH2:7][C:6]([O-:45])=[O:5])[C:17]([C:18]([F:20])([F:19])[F:21])=[CH:16][N:15]=3)=[CH:28][CH:27]=2)[CH2:30]1)=[O:35])([CH3:40])([CH3:38])[CH3:39].[Li+:2]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 71208999HCID 71208999, compound

Product 1

HCID 68282864HCID 68282864, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiOH.H2O (0.015 g, 0.65 mmol, 3 eq) was added to a solution of tert-butyl 3-(4-((4-(2-(2-methoxy-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)pyrrolidine-1-carboxylate (I139) (0.13 g, 0.22 mmol) in THF (7 mL), water (1.5 mL) and methanol (1 mL) and the resulting mixture was allowed to stir at room temperature for 70 hours. The volatiles were removed in vacuo and the residue was diluted with EtOAc (50 mL) and saturated aqueous NaHCO3 (50 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2×50 mL). The combined organic layers were washed with brine (50 mL), dried over MgSO4 and the solvent removed in vacuo to give the title compound (I140) (0.12 g, 99%) as a pale yellow oil; LCMS Method C: rt 6.56 min; m/z 571.1 [M−Li+2H]+, 515.1 [M−Li−tButyl+2H]+, 471.1 [M−Li−Boc+2H]+, 569.2 [M−Li−H]−.

Workup

  1. customThe volatiles were removed in vacuo
  2. additionthe residue was diluted with EtOAc (50 mL) and saturated aqueous NaHCO3 (50 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc (2×50 mL)
  5. washThe combined organic layers were washed with brine (50 mL)
  6. dry with materialdried over MgSO4
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-61da03bd8bdc40f484c40224bfdca95f
Source dataset
uspto-grants-2015_04
Patent number
US09012461B2

Reaction notes

Loading…