海萝胶 → 3-[N-(p-chlorobenzoyloxy)-N-formylamino] propylphosphonic acid

HRID 1706233

反应方程式

HRID 1706233 反应方程式
[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

参与物

9

反应物 4

HCID 313海萝胶HCID 572膦胺霉素HCID 8501对氯苯甲酰氯HCID 5360545钠

产物 1

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

试剂、催化剂与溶剂 4

HCID 180丙酮溶剂2 次HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 8857乙酸乙酯溶剂HCID 14798二甲基对苯二胺二盐酸溶剂

实验过程

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.).

后处理

  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.)

来源与证据

ORD记录
ord-298e2aeacd5c436fa4ceae627a011dfd
来源数据集
uspto-grants-1980_06
专利号
US04206156

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