Water → HCID 18991509, compound

HRID 487494Notes

Reaction equation

HRID 487494 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>C(Cl)Cl>[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

5

Reactant 3

HCID 962WaterHCID 68176Thionyl bromideHCID 18991588HCID 18991588, compound

Product 1

HCID 18991509HCID 18991509, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7.5 g (23.6 mmol) of ethyl 6-ethoxycarbonylmethoxy-2-formylamino-3-hydroxy-4-methylene-hexanoate are dissolved in 75 ml of CH2Cl2 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. customThe organic phase is separated
  2. washwashed once with water, once with a 1N solution of KHCO3 and once with brine
  3. extractionThe aqueous phases are extracted twice with CH2Cl2
  4. dry with materialThe combined organic phases are dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-79cfdf1076944a0c919ba5193b2a5651
Source dataset
uspto-grants-1994_03
Patent number
US05294734

Reaction notes

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