Water → HCID 53648515, compound

HRID 487486Notes

Reaction equation

HRID 487486 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 phases are dried over Na2SO4, filtered, and the filtrate is concentrated by evaporation giving ethyl 4-bromomethyl-7-ethoxycarbonylmethoxy-2-formylamino-hept-3-enoate as a yellow oil which is further reacted without purification. 6.4 g (15 mmol) of ethyl 4-bromomethyl-7-ethoxycarbonylmethoxy-2-formylamino-hept-3-enoate and 14.8 ml (60 mmol) of triisopropyl phosphite (90%) are heated to 80° C. and stirred for 18 hours under a pressure of 100 mbar. Excess triisopropyl phosphite is removed by distillation and the residue is chromatographed over silica gel with hexane/ethyl acetate (1:2:5%) to give ethyl 7-ethoxycarbonylmethoxy-2-formylamino-4-diisopropylphosphonomethyl-hept-3-enoate as a brown oil.

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 phases are dried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-89c13c0ea1b24c50a3cfcd0d5c6065ad
Source dataset
uspto-grants-1994_03
Patent number
US05294734

Reaction notes

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