Lithium Hydroxide → HCID 56654777, compound

HRID 2409179Notes

Reaction equation

HRID 2409179 reaction equation
[NH2:1][C:2]1[N:3]([CH3:31])[C:4](=[O:30])[C:5]([CH3:29])([CH3:28])[C@:6]([C:9]2[CH:10]=[C:11]([NH:16][CH:17]3[CH2:22][CH:21]4[CH2:23][CH:18]3[CH2:19][CH:20]4[O:24]C(=O)C)[CH:12]=[CH:13][C:14]=2[F:15])([CH3:8])[N:7]=1.[Li+].[OH-]>C1COCC1.CO.O>[NH2:1][C:2]1[N:3]([CH3:31])[C:4](=[O:30])[C:5]([CH3:29])([CH3:28])[C@:6]([C:9]2[CH:10]=[C:11]([NH:16][CH:17]3[CH2:22][CH:21]4[CH2:23][CH:18]3[CH2:19][CH:20]4[OH:24])[CH:12]=[CH:13][C:14]=2[F:15])([CH3:8])[N:7]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 66727426HCID 66727426, compound

Product 1

HCID 56654777HCID 56654777, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of acetic acid 5-[3-((S)-2-amino-1,4,5,5-tetramethyl-6-oxo-1,4,5,6-tetrahydro-pyrimidin-4-yl)-4-fluoro-phenylamino]-bicyclo[2.2.1]hept-2-yl ester (example 93, 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 dissolved in 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 separated, dried over Na2SO4 and evaporated to yield a mixture of isomers of the title compound as a colorless waxy solid. MS (ESI): m/z=389.3 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthe residue dissolved in aqueous HCl (0.5N) until pH=5
  3. washwashed with EtOAc
  4. extractionextracted with EtOAc
  5. customThe organic phase was separated
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customto yield

Sources & evidence

ORD record
ord-2bca681ec86640e6862c56f20440662e
Source dataset
uspto-grants-2014_08
Patent number
US08815881B2

Reaction notes

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