Water → HCID 53648515, compound

HRID 376153Notes

Reaction equation

HRID 376153 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][O:7][CH2:8][CH2:9][CH2:10][C:11](=[CH2:23])[CH:12](O)[CH:13]([NH:19][CH:20]=[O:21])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:5])[CH3:2].S(Br)([Br:26])=O.O>C(Cl)Cl>[Br:26][CH2:23][C:11]([CH2:10][CH2:9][CH2:8][O:7][CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:12][CH:13]([NH:19][CH:20]=[O:21])[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

5

Reactant 3

HCID 962WaterHCID 68176Thionyl bromideHCID 18991581HCID 18991581, compound

Product 1

HCID 53648515HCID 53648515, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5 g (15.1 mmol) of ethyl 7-ethoxycarbonylmethoxy-2-formylamino-3-hydroxy-4-methylene-heptanoate are dissolved in 50 ml of CH2Cl2 and 1.4 ml (18.1 mmol) of thionyl bromide are added dropwise at room temperature. After 2 hours 50 ml of water are added and the batch is stirred vigorously 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 once with CH2Cl2. The combined organic phases are dried over Na2SO4, filtered, and the filtrate is concentrated by evaporation giving ethyl 4-bromomethyl-7-ethoxycarbonyhnethoxy-2-formylamino-hept-3-enoate as a yellow 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 once with CH2Cl2
  4. dry with materialThe combined organic phases are dried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-d980dd8df9204e9ea6256a6e05fadf93
Source dataset
uspto-grants-1996_01
Patent number
US05488140

Reaction notes

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