Acetic Acid → HCID 57950708, compound

HRID 598906Notes

Reaction equation

HRID 598906 reaction equation
[CH3:1][C:2]1([CH3:32])[O:7][C:6](=[O:8])[CH:5]([C:9](=O)[C@@H:10]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:11][C:12]2[CH:13]=[N:14][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:17]=2)[C:4](=[O:31])[O:3]1.C(O)(=O)C.[BH4-].[Na+]>C(Cl)Cl>[CH3:1][C:2]1([CH3:32])[O:3][C:4](=[O:31])[CH:5]([CH2:9][C@@H:10]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])[CH2:11][C:12]2[CH:13]=[N:14][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:16][CH:17]=2)[C:6](=[O:8])[O:7]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 57950562HCID 57950562, compound

Product 1

HCID 57950708HCID 57950708, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-tert-Butyl 1-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-1-oxo-3-(6-(trifluoromethyl)pyridin-3-yl)propan-2-ylcarbamate in 100 mL DCM was cooled to −5° C. Acetic acid (4.45 g, 74.1 mmol) was added in one portion. The resulting mixture was stirred for 5 minutes and sodium borohydride (0.637 g, 16.8 mmol) was added portion-wise over 40 minutes. After stirring for another 40 minutes, the reaction mixture was washed with brine (3×150 mL) and water (2×100 mL). The organic layer was dried over MgSO4. After removing the solvent, the desired product compound (2.5 g, 83%) was obtained as a white solid. LCMS (API-ES) m/z (%): 447.0 (100%, M+H+).

Workup

  1. stirringAfter stirring for another 40 minutes
  2. washthe reaction mixture was washed with brine (3×150 mL) and water (2×100 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. customAfter removing the solvent

Sources & evidence

ORD record
ord-00393df1bd9e47ca8b24fcbb310125c5
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

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