N,N-Bis(trimethylsilyl)trifluoroacetamide → HCID 57948924, compound

HRID 1992270Notes

Reaction equation

HRID 1992270 reaction equation
[NH2:1][C@@:2]([C:7]1[CH:12]=[C:11]([Br:13])[C:10]([F:14])=[CH:9][C:8]=1[F:15])([CH3:6])[CH2:3][CH2:4][OH:5].C[Si](N([Si](C)(C)C)C(=O)C(F)(F)F)(C)C.[C:31]([N:39]=[C:40]=[S:41])(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C1COCC1>[C:31]([NH:39][C:40]([NH:1][C@@:2]([C:7]1[CH:12]=[C:11]([Br:13])[C:10]([F:14])=[CH:9][C:8]=1[F:15])([CH3:6])[CH2:3][CH2:4][OH:5])=[S:41])(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 65279N,N-Bis(trimethylsilyl)trifluoroacetamideHCID 68284Benzoyl isothiocyanateHCID 57948964HCID 57948964, compound

Product 1

HCID 57948924HCID 57948924, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-3-amino-3-(5-bromo-2,4-difluoro-phenyl)-butan-1-ol (9.5 g, 34 mmoles, 1 equiv) in THF (50 mL) is added bis(trimethylsilyl)trifluoroacetamide (8.7 g, 34 mmol, 1 equiv). After 2 h, benzoyl isothiocyanate (5.5 g, 34 mmoles, 1 equiv) is added dropwise. The reaction is stirred 18 h, quenched with water, and extracted with ethyl acetate. The combined organic phases are extracted with 1 N HCl and saturated aqueous NaCl. The organic phase is dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the title compound (>95% yield, 90% purity as determined by LCMS): MS (m/z): 443, 445 (M+1).

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate
  3. extractionThe combined organic phases are extracted with 1 N HCl and saturated aqueous NaCl
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f0533f1298124d3ca3d1edbf46b90ca2
Source dataset
uspto-grants-2010_01
Patent number
US07648983B2

Reaction notes

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