Potassium tert-butoxide → HCID 86668086, compound

HRID 474116Notes

Reaction equation

HRID 474116 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C@@:8]([NH:14][C:15](=[O:18])[CH2:16]Cl)([CH2:12][OH:13])[CH:9]([F:11])[F:10])[C:5]([F:19])=[C:4]([Si](CC)(CC)CC)[CH:3]=1.CC(C)([O-])C.[K+]>C(O)(C)(C)C.C(OCC)(=O)C>[Br:1][C:2]1[N:7]=[C:6]([C@@:8]2([CH:9]([F:11])[F:10])[NH:14][C:15](=[O:18])[CH2:16][O:13][CH2:12]2)[C:5]([F:19])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 86668084HCID 86668084, compound

Product 1

HCID 86668086HCID 86668086, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of N—[(R)-1-(6-bromo-3-fluoro-4-triethylsilanyl-pyridin-2-yl)-2,2-difluoro-1-hydroxymethyl-ethyl]-2-chloro-acetamide (2.32 g, 4.88 mmol) in t-butanol (50 ml) was added potassium tert-butoxide (7.31 ml, 7.31 mmol, 1M in THF) and the solution was stirred in a closed vial for 18 h at 100° C. The reaction mixture was diluted with ethyl acetate, washed with water, sat. NaHSO4 solution and brine, dried over sodium sulfate, filtered and evaporated. The crude product (2.36 g) was chromatographed over silica gel (24 g redisep column, cyclohexane/ethyl acetate 10-80%) to give the title compound. 1.13 g (71% yield). Triethylsilylated lactam (640 mg) was recovered.

Workup

  1. washwashed with water, sat. NaHSO4 solution and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product (2.36 g) was chromatographed over silica gel (24 g redisep column, cyclohexane/ethyl acetate 10-80%)

Sources & evidence

ORD record
ord-e50b99160ca74b79bb3cab8be4f2823c
Source dataset
uspto-grants-2014_01
Patent number
US08637508B2

Reaction notes

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