Triethylamine → HCID 90157006, compound

HRID 1486760Notes

Reaction equation

HRID 1486760 reaction equation
[F:1][CH:2]([F:8])[CH:3]([OH:7])[C:4]([NH2:6])=[O:5].[C:9]([Si:13]([CH3:16])([CH3:15])Cl)([CH3:12])([CH3:11])[CH3:10].C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[Si:13]([O:7][CH:3]([CH:2]([F:8])[F:1])[C:4]([NH2:6])=[O:5])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 90157399HCID 90157399, compound

Product 1

HCID 90157006HCID 90157006, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3,3-difluoro-2-hydroxypropanamide (700 mg, 5.6 mmol) in DMF (5.6 mL) was added tert-butyldimethylchlorosilane (1.10 g, 7.28 mmol) and triethylamine (1.17 mL, 8.40 mmol). The mixture was stirred at room temperature for 3 h, diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate (2×) and brine. The organic layer was dried over sodium sulfate, filtered, and concentrated to provide Intermediate 10 that was used without further purification. MS: m/z=240.3 (M+H).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate (2×) and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e1a66ad5f6fd4aee8c5cacdae944dfc5
Source dataset
uspto-grants-2016_08
Patent number
US09428492B2

Reaction notes

Loading…