Fosmidomycin → 3-(N-benzoyloxy-N-formylamino)propylphosphonic acid

HRID 1706232

반응식

HRID 1706232 반응식
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na].[CH:11]([N:13]([CH2:15][CH2:16][CH2:17][P:18](=[O:21])([OH:20])[OH:19])[OH:14])=[O:12].[OH-].[Na+]>CC(C)=O.O>[C:1]([O:14][N:13]([CH2:15][CH2:16][CH2:17][P:18](=[O:20])([OH:19])[OH:21])[CH:11]=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 572FosmidomycinHCID 7412Benzoyl chlorideHCID 14798Sodium HydroxideHCID 5360545Sodium

생성물 1

HCID 203372243-(N-benzoyloxy-N-formylamino)propylphosphonic acid수율 48.2%

시약·촉매·용매 2

HCID 180Acetone용매2회HCID 962Water용매

실험 절차

A solution of benzoyl chloride (700 mg) in dry acetone (6 ml) was added dropwise to a solution of sodium salt of 3-(N-formyl-N-hydroxyamino)propylphosphonic acid (820 mg) in a mixture of water (15 ml) and acetone (15 ml) under ice-cooling, while stirring. During this period, pH of the mixture was kept at around 7.5-7.7 with 1 N aqueous sodium hydroxide solution. The stirring was continued at the same temperature for 10 minutes and then acetone was evaporated under reduced pressure. The resulting aqueous solution was adjusted to pH 3.5 with 1N hydrochloric acid and ether (40 ml) was added thereto. After removal of the precipitated impurities, the aqueous layer was adjusted to pH 1.6 with 1N hydrochloric acid and extracted three times with ethyl acetate (50 ml, 20 ml×2). The combined ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and evaporated to dryness to give crystals, which were washed with ether to give crystalline 3-(N-benzoyloxy-N-formylamino)propylphosphonic acid (620 mg). Mp 149°-153° C. (dec.).

후처리

  1. temperaturecooling
  2. waitDuring this period
  3. customacetone was evaporated under reduced pressure
  4. additionwas added
  5. customAfter removal of the precipitated impurities
  6. extractionextracted three times with ethyl acetate (50 ml, 20 ml×2)
  7. washThe combined ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. customevaporated to dryness
  10. customto give crystals, which
  11. washwere washed with ether

출처 및 근거

ORD 기록
ord-430cd1d575fa4a45a8f3c406116ad0ac
출처 데이터셋
uspto-grants-1980_06
특허 번호
US04206156

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