Lithium Hydroxide → 2-(2-(2-(2-(4-(1-(tert-Butoxycarbonylamino)ethyl)phenylamino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetic acid

HRID 1779030Notes

Reaction equation

HRID 1779030 reaction equation
[Li+].[OH-].[C:3]([O:7][C:8]([NH:10][CH:11]([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)[CH3:12])=[O:9])([CH3:6])([CH3:5])[CH3:4]>C1COCC1.O>[C:3]([O:7][C:8]([NH:10][CH:11]([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:42])([F:41])[F:40])=[CH:22][N:21]=2)=[CH:17][CH:18]=1)[CH3:12])=[O:9])([CH3:4])([CH3:5])[CH3:6]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86712678Methyl 2-(2-(2-(2-(4-(1-(tert-butoxycarbonylamino)ethyl)phenylamino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetate

Product 1

HCID 867126792-(2-(2-(2-(4-(1-(tert-Butoxycarbonylamino)ethyl)phenylamino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiOH (69.0 mg, 2.86 mmol) was added to a solution of methyl 2-(2-(2-(2-(4-(1-(tert-butoxycarbonylamino)ethyl)phenylamino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetate (A65) (320 mg, 0.573 mmol) in THF (7.5 mL) and water (2.5 mL) and the resulting mixture stirred at room temperature overnight. The resulting mixture was evaporated in vacuo then the residue was partitioned between EtOAc (15 mL) and 1 M aqueous HCl. The phases were separated and the aqueous phase was extracted with EtOAc. The combined organic phases were washed with brine, dried with Na2SO4 and concentrated to give the title compound A66 (310 mg, 99%); LCMS-B: rt 8.30 min; m/z 545.4 [M+H]+.

Workup

  1. customThe resulting mixture was evaporated in vacuo
  2. customthe residue was partitioned between EtOAc (15 mL) and 1 M aqueous HCl
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with EtOAc
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4de4ac2c26634bc8a9d9b4b717d52904
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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