Hydrochloric Acid → 3-[N-(p-chlorobenzoyloxy)-N-formylamino] propylphosphonic acid

HRID 1706233

反応式

HRID 1706233 の反応式
[Na].[CH:2]([N:4]([CH2:6][CH2:7][CH2:8][P:9](=[O:12])([OH:11])[OH:10])[OH:5])=[O:3].[Cl:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1.Cl>[OH-].[Na+].O.CC(C)=O.C(OCC)(=O)C>[Cl:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([O:5][N:4]([CH2:6][CH2:7][CH2:8][P:9](=[O:11])([OH:10])[OH:12])[CH:2]=[O:3])=[O:19])=[CH:16][CH:15]=1

参加物

9

反応物 4

HCID 313Hydrochloric AcidHCID 572FosmidomycinHCID 85014-Chlorobenzoyl chlorideHCID 5360545Sodium

生成物 1

HCID 203372273-[N-(p-chlorobenzoyloxy)-N-formylamino] propylphosphonic acid収率 75.3%

試薬・触媒・溶媒 4

HCID 180Acetone溶媒2 回HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

Monosodium salt of 3-(N-formyl-N-hydroxyamino)propylphosphonic acid (2.05 g.) was dissolved in a mixture of 1 N aqueous sodium hydroxide solution (20 ml.), water (10 ml.) and acetone (10 ml.). To the solution was added dropwise a solution of p-chlorobenzoyl chloride (2.10 g.) in dry acetone (5 ml.) at 0°-5° C. with stirring. After the stirring was continued at the same temperature for 30 minutes, ethyl acetate (40 ml.) was added to the reaction mixture and then the resultant mixture was adjusted to pH 1 with 10% hydrochloric acid. The ethyl acetate layer was separated and then the aqueous layer was extracted again with ethyl acetate (20 ml.). The combined ethyl acetate layer was washed with aqueous sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure to give an oily residue, which was crystallized with ethylether (40 ml.) to give crystals. The crystals were separated by filtration, washed twice with ethylether (10 ml.) to give crystalline 3-[N-(p-chlorobenzoyloxy)-N-formylamino] propylphosphonic acid (2.71 g.).

後処理

  1. customThe ethyl acetate layer was separated
  2. extractionthe aqueous layer was extracted again with ethyl acetate (20 ml.)
  3. washThe combined ethyl acetate layer was washed with aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give an oily residue, which
  7. customwas crystallized with ethylether (40 ml.)
  8. customto give crystals
  9. customThe crystals were separated by filtration
  10. washwashed twice with ethylether (10 ml.)

出典と根拠

ORDレコード
ord-298e2aeacd5c436fa4ceae627a011dfd
出典データセット
uspto-grants-1980_06
特許番号
US04206156

関連ノート

読み込み中…