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

HRID 376113Notes

Reaction equation

HRID 376113 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-08b0b4accb724ef9b65db4bb91f7e545
Source dataset
uspto-grants-1996_01
Patent number
US05488140

Reaction notes

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