Water → 4-Bromomethyl-2-formylamino-6-methoxy-hex-3-enoic acid ethyl ester

HRID 487448Notes

Reaction equation

HRID 487448 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH:5]([NH:14][CH:15]=[O:16])[CH:6](O)[C:7](=[CH2:12])[CH2:8][CH2:9][O:10][CH3:11])[CH3:2].S(Br)([Br:20])=O.O>ClCCCl>[CH2:1]([O:3][C:4](=[O:17])[CH:5]([NH:14][CH:15]=[O:16])[CH:6]=[C:7]([CH2:12][Br:20])[CH2:8][CH2:9][O:10][CH3:11])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 68176Thionyl bromideHCID 543412892-Formylamino-3-hydroxy-6-methoxy-4-methylene-hexanoic acid ethyl ester

Product 1

HCID 544285944-Bromomethyl-2-formylamino-6-methoxy-hex-3-enoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

19.0 g (77.5 mmol) of 2-formylamino-3-hydroxy-6-methoxy-4-methylene-hexanoic acid ethyl ester are dissolved in 190 ml of 1,2-dichloroethane, and 7.20 ml (93.0 mmol) of thionyl bromide are added dropwise at room temperature. After 45 minutes, 100 ml of water are added and the mixture is stirred vigorously for 10 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-2-formylamino-6-methoxy-hex-3-enoic acid ethyl ester is obtained in the form of a reddish-brown 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-fef5e06a094e4d929e26d7d5f5a82572
Source dataset
uspto-grants-1994_03
Patent number
US05294734

Reaction notes

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