Water → HCID 54470496, compound

HRID 487437Notes

Reaction equation

HRID 487437 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH:5]([NH:16][CH:17]=[O:18])[CH:6](O)[C:7](=[CH2:14])[CH2:8][CH2:9][O:10][C:11](=[O:13])[CH3:12])[CH3:2].S(Br)([Br:22])=O.O>ClCCl>[CH2:1]([O:3][C:4](=[O:19])[CH:5]([NH:16][CH:17]=[O:18])[CH:6]=[C:7]([CH2:14][Br:22])[CH2:8][CH2:9][O:10][C:11](=[O:13])[CH3:12])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 68176Thionyl bromideHCID 54292130HCID 54292130, compound

Product 1

HCID 54470496HCID 54470496, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

9.19 g (35.9 mmol) of 6-acetoxy-2-formylamino-3-hydroxy-4-methylene-hexanoic acid ethyl ester are dissolved in 100 ml of dichloromethane, and 3.34 ml (43.1 mmol) of thionyl bromide are added dropwise at room temperature. After one hour, 10 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, saturated potassium hydrogen carbonate solution and again with water, dried over magnesium sulfate, filtered and concentrated by evaporation. 6-acetoxy-4-bromomethyl-2-formylamino-hex-3-enoic acid ethyl ester is obtained in the form of a brownish oil.

Workup

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

Sources & evidence

ORD record
ord-c7647916160045dba0d6a22bdcef35b0
Source dataset
uspto-grants-1994_03
Patent number
US05294734

Reaction notes

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