Water → HCID 53734087, compound

HRID 487461Notes

Reaction equation

HRID 487461 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH:5]([NH:17][CH:18]=[O:19])[CH:6](O)[C:7](=[CH2:15])[CH2:8][CH2:9][CH2:10][O:11][C:12](=[O:14])[CH3:13])[CH3:2].S(Br)([Br:23])=O.O>ClCCl>[CH2:1]([O:3][C:4](=[O:20])[CH:5]([NH:17][CH:18]=[O:19])[CH:6]=[C:7]([CH2:15][Br:23])[CH2:8][CH2:9][CH2:10][O:11][C:12](=[O:14])[CH3:13])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 68176Thionyl bromideHCID 540452357-Acetoxy-2-formylamino-3-hydroxy-4-methylene-heptanoic acid ethyl ester

Product 1

HCID 53734087HCID 53734087, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.9 g (20.5 mmol) of 7-acetoxy-2-formylamino-3-hydroxy-4-methylene-heptanoic acid ethyl ester are dissolved in 60 ml of dichloromethane, and 1.9 ml (24.6 mmol) of thionyl bromide are added dropwise at room temperature. After one hour, 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, 1N KHCO3 solution and again with water, dried over MgSO4, filtered and concentrated by evaporation. 7-acetoxy-4-bromomethyl-2-formylamino-hept-3-enoic acid ethyl ester is obtained in the form of a brown oil, which is reacted further in the crude state.

Workup

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

Sources & evidence

ORD record
ord-a5ce58ddb30f47fab778f18ce2251e5e
Source dataset
uspto-grants-1994_03
Patent number
US05294734

Reaction notes

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