Water → HCID 54531862, compound

HRID 376117Notes

Reaction equation

HRID 376117 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH:5]([NH:13][CH:14]=[O:15])[CH:6](O)[C:7](=[CH2:11])[CH2:8][CH2:9][F:10])[CH3:2].S(Br)([Br:19])=O.O>ClCCCl>[CH2:1]([O:3][C:4](=[O:16])[CH:5]([NH:13][CH:14]=[O:15])[CH:6]=[C:7]([CH2:11][Br:19])[CH2:8][CH2:9][F:10])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 68176Thionyl bromideHCID 54151003HCID 54151003, compound

Product 1

HCID 54531862HCID 54531862, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

1.40 g (6.0 mmol) of 6-fluoro-2-formylamino-3-hydroxy-4-methylene-hexanoic acid ethyl ester are dissolved in 14 ml of 1,2-dichloroethane, and 0.56 ml (7.2 mmol) of thionyl bromide is added dropwise at room temperature. After 45 minutes, 12 ml of water are added and the mixture is stirred vigorously for 15 minutes. The organic phase is separated off, washed in succession with water, 1N potassium hydrogen carbonate solution and again with water, dried over sodium sulfate, filtered and concentrated by evaporation. 4-bromomethyl-6-fluoro-2-formylamino-hex-3-enoic acid ethyl ester is obtained in the form of a brownish-yellow oil.

Workup

  1. customThe organic phase is separated off
  2. washwashed in succession with water, 1N potassium hydrogen carbonate solution and again with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-2919700347fa49738461f928dc771247
Source dataset
uspto-grants-1996_01
Patent number
US05488140

Reaction notes

Loading…