Ethanol → HCID 10926216, compound

HRID 975486Notes

Reaction equation

HRID 975486 reaction equation
ClC(O[CH2:5][CH:6](C)C)=O.[C:9]([O:13][C:14]([NH:16][CH2:17][P:18]([CH2:21][NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])(=[O:20])[OH:19])=[O:15])([CH3:12])([CH3:11])[CH3:10].C(O)C.C(N(CC)CC)C>C(Cl)Cl>[C:9]([O:13][C:14]([NH:16][CH2:17][P:18]([CH2:21][NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])(=[O:19])[O:20][CH2:5][CH3:6])=[O:15])([CH3:12])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 11120883HCID 11120883, compound

Product 1

HCID 10926216HCID 10926216, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Isobutyl chloroformate (1.50 ml, 11.48 mmol) is added dropwise with stirring at 0° C. to a solution of the phosphinic acid 1 (3.200 g, 9.88 mmol) in a mixture of methylene chloride (50 ml), ethanol (3.00 ml, 51.59 mmol), triethylamine (1.40 ml, 10.06 mmol) and N,N-dimethylpyridine (10 mg). After 90 minutes, the reaction solution is extracted with saturated aqueous ammonium chloride solution (30 ml) and saturated aqueous KHCO3 solution (30 ml). The organic phase is dried over Na2SO4 and concentrated under reduced pressure. After purification by column chromatography on silica gel (ethyl acetate/heptane=3:2), the phosphinic acid ester 3 (1.840 g, 53% of theory) is obtained. See above spectroscopic data.

Workup

  1. extractionthe reaction solution is extracted with saturated aqueous ammonium chloride solution (30 ml) and saturated aqueous KHCO3 solution (30 ml)
  2. dry with materialThe organic phase is dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customAfter purification by column chromatography on silica gel (ethyl acetate/heptane=3:2)

Sources & evidence

ORD record
ord-6a0af0fb985c4d0386328b373eb6fb1a
Source dataset
uspto-grants-1997_03
Patent number
US05608098

Reaction notes

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