Lithium Hydroxide → HCID 57516123, compound

HRID 2409185Notes

Reaction equation

HRID 2409185 reaction equation
C([O:3][C:4](=[O:33])[CH2:5][CH:6]1[CH2:10][CH2:9][CH:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[C:14]([C@:19]3([CH3:30])[C:24]([CH3:26])([CH3:25])[C:23](=[O:27])[N:22]([CH3:28])[C:21]([NH2:29])=[N:20]3)[CH:13]=2)[C:7]1([CH3:32])[CH3:31])C.[Li+].[OH-]>C1COCC1.CO.O>[NH2:29][C:21]1[N:22]([CH3:28])[C:23](=[O:27])[C:24]([CH3:26])([CH3:25])[C@:19]([C:14]2[CH:13]=[C:12]([NH:11][CH:8]3[CH2:9][CH2:10][CH:6]([CH2:5][C:4]([OH:33])=[O:3])[C:7]3([CH3:31])[CH3:32])[CH:17]=[CH:16][C:15]=2[F:18])([CH3:30])[N:20]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 57516116HCID 57516116, compound

Product 1

HCID 57516123HCID 57516123, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {3-[3-((S)-2-amino-1,4,5,5-tetramethyl-6-oxo-1,4,5,6-tetrahydro-pyrimidin-4-yl)-4-fluoro-phenylamino]-2,2-dimethyl-cyclopentyl}-acetic acid ethyl ester (example 98, 0.05 mmole) in THF (1 ml), MeOH (0.3 ml) and H2O (0.3 ml) was added LiOH (1N, 0.1 mmole) and the reaction mixture was stirred at room temperature for 4 h. The mixture was concentrated in vacuo, the residue was diluted with aqueous HCl (0.5N) until pH=5 and washed with EtOAc. The aqueous phase was basified to pH=8 with a saturated aqueous NaHCO3 solution and extracted with EtOAc. The organic phase was dried over Na2SO4 and evaporated to yield a mixture of isomers of the title compound as a white solid. MS (ESI): m/z=433.5 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionthe residue was diluted with aqueous HCl (0.5N) until pH=5
  3. washwashed with EtOAc
  4. extractionextracted with EtOAc
  5. dry with materialThe organic phase was dried over Na2SO4
  6. customevaporated
  7. customto yield

Sources & evidence

ORD record
ord-55e71b33d69b4a8da604b7d58a612b14
Source dataset
uspto-grants-2014_08
Patent number
US08815881B2

Reaction notes

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