Thionyl bromide → HCID 18991509, compound

HRID 376160Notes

Reaction equation

HRID 376160 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][O:7][CH2:8][CH2:9][C:10](=[CH2:22])[CH:11]([OH:21])[CH:12]([NH:18][CH:19]=[O:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:5])[CH3:2].S(Br)([Br:25])=O>O>[Br:25][CH2:22][CH:10]([CH2:9][CH2:8][O:7][CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:11]([OH:21])[CH:12]([NH:18][CH:19]=[O:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

4

Reactant 2

HCID 68176Thionyl bromideHCID 18991588HCID 18991588, compound

Product 1

HCID 18991509HCID 18991509, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7.5 g (23.6 mmol)of ethyl 6-ethoxycarbonylmethoxy-2-formylamino-3-hydroxy-4-methylene-hexanoate are dissolved in 75 ml of CH2C12 and 2.2 ml (28.3 mmol) of thionyl bromide are then added dropwise at room temperature to this solution. After 1 hour 50 ml of water are added and the reaction mixture is stirred vigorously for 10 minutes. The organic phase is separated and washed once with water, once with a 1N solution of KHCO3 and once with brine. The aqueous phases are extracted twice with CH2Cl2. The combined organic phases are dried over Na2SO4, filtered, and concentrated by evaporation giving ethyl 4-bromomethyl-6-ethoxycarbonylmethoxy-2-formylamino-3-hydroxy-hexanoate as a yellow oil which is further reacted without purification.

Workup

  1. additionare then added dropwise at room temperature to this solution
  2. customThe organic phase is separated
  3. washwashed once with water, once with a 1N solution of KHCO3 and once with brine
  4. extractionThe aqueous phases are extracted twice with CH2Cl2
  5. dry with materialThe combined organic phases are dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-aebe0c3fd5fc42b89b89eb71112d47aa
Source dataset
uspto-grants-1996_01
Patent number
US05488140

Reaction notes

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