Water → HCID 53645081, compound

HRID 376131Notes

Reaction equation

HRID 376131 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][N:10]([C:12](=[O:14])[CH3:13])[CH3:11])[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][N:10]([C:12](=[O:14])[CH3:13])[CH3:11])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 68176Thionyl bromideHCID 53808936HCID 53808936, compound

Product 1

HCID 53645081HCID 53645081, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

15.8 g (55.2 mmol) of 6-(N-acetyl-N-methylamino)-2-formylamino-3-hydroxy-4-methylene-hexanoic acid ethyl ester are dissolved in 150 ml of dichloromethane, and 5.1 ml (66.2 mmol) of thionyl bromide are added dropwise at room temperature. After one hour, 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 KHCO3 solution and again with water, dried over MgSO4, filtered and concentrated by evaporation. 6-(N-acetyl-N-methylamino)-4-bromomethyl-2-formylamino-hex-3-enoic acid ethyl ester is obtained in the form of a yellowish-orange 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-e59b4ce968eb446b9a93236feb50ac00
Source dataset
uspto-grants-1996_01
Patent number
US05488140

Reaction notes

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