Water → HCID 54248109, compound

HRID 376169Notes

Reaction equation

HRID 376169 reaction equation
[C:1]([O:4][CH:5]([CH3:20])[CH2:6][C:7](=[CH2:19])[CH:8](O)[CH:9]([NH:15][CH:16]=[O:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:3])[CH3:2].S(Br)([Br:23])=O.O>C(Cl)Cl>[C:1]([O:4][CH:5]([CH3:20])[CH2:6][C:7]([CH2:19][Br:23])=[CH:8][CH:9]([NH:15][CH:16]=[O:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 68176Thionyl bromideHCID 18991601HCID 18991601, compound

Product 1

HCID 54248109HCID 54248109, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

17.0 g (59.1 mmol) of ethyl 6-acetoxy-2-formylamino-3-hydroxy-4-methylene-heptanoate are dissolved in 170 ml of CH2Cl2 and 5.5 ml (71 mmol) of thionyl bromide are then added dropwise at room temperature. After 1 hour, 100 ml of water are added and the batch is vigorously stirred for 10 minutes. The organic phase is separated and washed once with water, once with a 1N solution of KHCO3 and twice with water. The aqueous phases are extracted twice with CH2Cl2. The combined organic phases are dried over MgSO4, filtered and concentrated by evaporation, giving ethyl 6-acetoxy-4-bromomethyl-2-formylamino-hept-3-enoate as a brown oil which is further reacted without purification.

Workup

  1. customThe organic phase is separated
  2. washwashed once with water, once with a 1N solution of KHCO3 and twice with water
  3. extractionThe aqueous phases are extracted twice with CH2Cl2
  4. dry with materialThe combined organic phases are dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-11bbee00b80e48cd93134752ab12e08f
Source dataset
uspto-grants-1996_01
Patent number
US05488140

Reaction notes

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