Hydrochloric Acid → HCID 76831082, compound

HRID 1186169Notes

Reaction equation

HRID 1186169 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:18])=[C:6]([C:8]2([NH:13][C:14](=[O:17])[CH2:15]Cl)[CH2:10][CH:9]2[CH2:11][OH:12])[CH:7]=1.CC(C)([O-])C.[K+].Cl>C(O)(C)(C)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:18])=[C:6]([C:8]23[CH2:10][CH:9]2[CH2:11][O:12][CH2:15][C:14](=[O:17])[NH:13]3)[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 76831232HCID 76831232, compound

Product 1

HCID 76831082HCID 76831082, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
23 °C

Procedure

To a suspension of N-[(1SR,2RS)-1-(5-bromo-2-fluoro-phenyl)-2-hydroxymethyl-cyclopropyl]-2-chloro-acetamide (intermediate B9A) (495 mg, 1.47 mmol) in tert-butanol (6 ml) at 23° C. was added potassium tert-butoxide (KOBut) (550 mg, 4.9 mmol) in one portion [exothermic] and the mixture was stirred at 23° C. for 19 h. Poured into 1 M HCl, extracted with ethyl acetate, washed organic layer with brine, dried over sodium sulfate. Removal of the solvent in vacuum left an orange oil, which was purified by silica gel column chromatography with n-heptane/ethyl acetate to give the title compound as a white gum (405 mg, 92%). MS (ISP): m/z=300.1 [(M+H)−] and 302.2 [(M+2+H)+].

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed organic layer with brine
  3. dry with materialdried over sodium sulfate
  4. customRemoval of the solvent in vacuum
  5. waitleft an orange oil, which
  6. customwas purified by silica gel column chromatography with n-heptane/ethyl acetate

Sources & evidence

ORD record
ord-f1acd06d7f6c4fc6a5f94578863712b0
Source dataset
uspto-grants-2014_03
Patent number
US08673894B2

Reaction notes

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