Water → HCID 54073257, compound

HRID 376138Notes

Reaction equation

HRID 376138 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH:5]([NH:20][CH:21]=[O:22])[CH:6](O)[C:7](=[CH2:18])[CH2:8][CH2:9][O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:2].S(Br)([Br:26])=O.O>ClCCl>[CH2:1]([O:3][C:4](=[O:23])[CH:5]([NH:20][CH:21]=[O:22])[CH:6]=[C:7]([CH2:18][Br:26])[CH2:8][CH2:9][O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 68176Thionyl bromideHCID 54341833HCID 54341833, compound

Product 1

HCID 54073257HCID 54073257, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7.0 g (21.8 mmol) of 6-benzyloxy-2-formylamino-3-hydroxy-4-methylene-hexanoic acid ethyl ester are dissolved in 70 ml of dichloromethane, and 2.0 ml (26.1 mmol) of thionyl bromide are added dropwise at room temperature. After 2 hours, 40 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, N-KHCO3 solution and again with water, dried over MgSO4, filtered and concentrated by evaporation. 6-benzyloxy-4-bromomethyl-2-formylamino-hex-3-enoic acid ethyl ester is obtained in the form of a reddish-brown oil which can be reacted further without purification.

Workup

  1. customThe organic phase is separated off
  2. washwashed in succession with water, N-KHCO3 solution and again with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-c8e310706b224c5e8b5294d4cc2cbeb0
Source dataset
uspto-grants-1996_01
Patent number
US05488140

Reaction notes

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