Methanol → (S)-N-[1-[[(Dimethoxyphosphinyl)amino]carbonyl]-2-oxo-3-azetidinyl]benzeneacetamide

HRID 1380805

반응식

HRID 1380805 반응식
[O:1]=[C:2]1[C@@H:5]([NH:6][C:7](=[O:15])[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][NH:3]1.[CH2:16](COC)[O:17]C.C(Cl)Cl.[P:25](Cl)(Cl)([N:27]=[C:28]=[O:29])=[O:26].[CH3:32][OH:33]>N1C=CC=CC=1.C(N(CC)CC)C>[CH3:32][O:33][P:25]([NH:27][C:28]([N:3]1[CH2:4][C@H:5]([NH:6][C:7](=[O:15])[CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:2]1=[O:1])=[O:29])([O:17][CH3:16])=[O:26]

참가 물질

8

반응물 5

HCID 887MethanolHCID 6344DichloromethaneHCID 80711,2-DimethoxyethaneHCID 70090Phosphorisocyanatidic dichlorideHCID 13212049(S)-3-[[(phenylmethyl)carbonyl]amino]-2-azetidinone

생성물 1

HCID 13729268(S)-N-[1-[[(Dimethoxyphosphinyl)amino]carbonyl]-2-oxo-3-azetidinyl]benzeneacetamide

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 8471Triethylamine용매

반응 조건

온도
6 °C

실험 절차

A mixture of 105.6 mg (0.518 mmol) of (S)-N-(2-oxo-3-azetidinyl)benzeneacetamide, produced as in Example I, 6 mL of dimethoxyethane, and 2 mL of CH2Cl2 was stirred and cooled to 6° C.; 0.084 mL (0.776 mmol) of phosphorisocyanatidic dichloride was added, and stirring continued at 6°. After 15 minutes complete solution resulted. After an additional 45 minutes at 6° C., the mixture was cooled to -15°, and a solution of 0.216 mL of triethylamine, 0.125 mL of pyridine, and 1.5 mL of methanol was added. The resulting solution was stirred 1.5 hours at room temperature, and then concentrated under reduced pressure. A solution of the residue in CH2Cl2 was washed sequentially with water, 1N HCl, and brine, dried (MgSO4), treated with charcoal, filtered, and concentrated to dryness under reduced pressure. The residue was triturated with two 4 mL portions of ether, the ether decanted, and residual solvent removed from the remaining oil under reduced pressure to leave 72 mg of product.

후처리

  1. stirringstirring
  2. customcontinued at 6°
  3. customAfter 15 minutes complete solution resulted
  4. temperaturethe mixture was cooled to -15°
  5. stirringThe resulting solution was stirred 1.5 hours at room temperature
  6. concentrationconcentrated under reduced pressure
  7. washA solution of the residue in CH2Cl2 was washed sequentially with water, 1N HCl, and brine
  8. dry with materialdried (MgSO4)
  9. additiontreated with charcoal
  10. filtrationfiltered
  11. concentrationconcentrated to dryness under reduced pressure
  12. customThe residue was triturated with two 4 mL portions of ether
  13. customthe ether decanted
  14. customresidual solvent removed from the remaining oil under reduced pressure

출처 및 근거

ORD 기록
ord-c9ea77dcfbf04221a098f8e6d22965dc
출처 데이터셋
uspto-grants-1986_04
특허 번호
US04584132

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