Lithium hydroxide, monohydrate → HCID 86712640, compound

HRID 1778970Notes

Reaction equation

HRID 1778970 reaction equation
O[Li].O.[C:4]([O:8][C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]2[N:25]=[C:24]([CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH2:34][C:35]([O:37]C)=[O:36])[C:23]([C:39]([F:42])([F:41])[F:40])=[CH:22][N:21]=2)=[CH:15][CH:14]=1)=[O:10])([CH3:7])([CH3:6])[CH3:5]>CO.O.C1COCC1>[C:4]([O:8][C:9]([NH:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([NH:19][C:20]2[N:25]=[C:24]([CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH2:34][C:35]([OH:37])=[O:36])[C:23]([C:39]([F:41])([F:42])[F:40])=[CH:22][N:21]=2)=[CH:17][CH:18]=1)=[O:10])([CH3:7])([CH3:5])[CH3:6]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86712639HCID 86712639, compound

Product 1

HCID 86712640HCID 86712640, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiOH.H2O (94 mg, 2.2 mmol) was added to a solution of methyl 2-(2-(2-(2-((4-(((tert-butoxycarbonyl)amino)methyl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetate (A14) (306 mg, 0.562 mmol) in MeOH (1 mL), water (1 mL) and THF (10 mL) and the resulting mixture was stirred at room temperature overnight. The volatiles were removed in vacuo and the resultant oil partitioned between EtOAc (150 mL) and 2 M aqueous NaOH (100 mL). The organic layer was separated, washed with water (2×100 mL), brine (50 mL) and dried over MgSO4. The volatiles were removed in vacuo to yield the title compound A15 as a yellow oil (0.25 g, 83%); LCMS-A: rt 6.267 min; m/z 531 [M+H]+.

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe resultant oil partitioned between EtOAc (150 mL) and 2 M aqueous NaOH (100 mL)
  3. customThe organic layer was separated
  4. washwashed with water (2×100 mL), brine (50 mL)
  5. dry with materialdried over MgSO4
  6. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-caa664642e214922af648988249c30d0
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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