Water → HCID 54248109, compound

HRID 487503Notes

Reaction equation

HRID 487503 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-1eb8e135a1b54282b4f4dec1d903fbf3
Source dataset
uspto-grants-1994_03
Patent number
US05294734

Reaction notes

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