Water → HCID 20337234, compound

HRID 1706182Notes

Reaction equation

HRID 1706182 reaction equation
Br[CH2:2]/[CH:3]=[CH:4]/[P:5](=[O:12])([O:9][CH2:10][CH3:11])[O:6][CH2:7][CH3:8].[CH2:13]([O:15][C:16]([O:18][NH:19][C:20](=[O:24])[O:21][CH2:22][CH3:23])=[O:17])[CH3:14].O>CN(C)C=O.C(OCC)(=O)C.C(Cl)(Cl)Cl>[CH2:22]([O:21][C:20]([N:19]([CH2:2]/[CH:3]=[CH:4]/[P:5](=[O:12])([O:9][CH2:10][CH3:11])[O:6][CH2:7][CH3:8])[O:18][C:16]([O:15][CH2:13][CH3:14])=[O:17])=[O:24])[CH3:23]

Participants

7

Reactant 3

HCID 962WaterHCID 5702525Diethyl [(1E)-3-bromoprop-1-en-1-yl]phosphonateHCID 11446651Ethyl Ethoxycarbonyloxycarbamate

Product 1

HCID 20337234HCID 20337234, compoundYield 42.1%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of diethyl 3-bromo-trans-1-propenylphosphonate (23.83 g.) in N,N-dimethylformamide (50 ml.) was added dropwise to a suspension of ethyl N-ethoxycarbonyloxycarbamate (19.94 g.) in N,N-dimethylformamide (100 ml.) at -25°--30° C. in the course of 20 minutes. The reaction mixture was stirred at -20°--30° C. for an hour and at -5°--10° C. for an hour. Subsequently, the resultant mixture was poured int a mixture of water (1 liter) and ethyl acetate (0.7 l). The etheyl acetate layer was separated and the aqueous layer was extracted twice with ethyl acetate (300 ml.). The combined ethyl acetate layer was washed with water (300 ml.), dried over magnesium sulfate and concentrated under reduced pressure to give an oily residue (28.89 g.), which was subjected to a column chromatography on silica gel [Developing solvent: a mixture of chloroform and ethyl acetate (4:1)]. The eluate was concentrated under reduced pressure to give oily diethyl 3-(N-ethoxycarbonyl-N-ethoxycarbonyloxyamino)-trans-1-propenylphosphonate (13.80 g.).

Workup

  1. customThe etheyl acetate layer was separated
  2. extractionthe aqueous layer was extracted twice with ethyl acetate (300 ml.)
  3. washThe combined ethyl acetate layer was washed with water (300 ml.)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give an oily residue (28.89 g.), which
  7. concentrationThe eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-893c00ae9a0341e388e393cac5e7e04e
Source dataset
uspto-grants-1980_06
Patent number
US04206156

Reaction notes

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