4-Methylmorpholine → (3S)-alpha-[[(2-Oxo-3-azetidinyl)amino]carbonyl]benzeneacetic acid, phenylmethyl ester

HRID 371199노트

반응식

HRID 371199 반응식
[NH:1]1[CH2:4][CH2:3][C:2]1=[O:5].C[N:7]1CCOCC1.Cl[C:14]([CH:16]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])=[O:15]>CN(C)C=O.C(#N)C>[O:5]=[C:2]1[C@@H:3]([NH:7][C:14]([CH:16]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])=[O:15])[CH2:4][NH:1]1

참가 물질

6

반응물 3

HCID 79724-MethylmorpholineHCID 1367212-AzetidinoneHCID 21289869Benzyl (chlorocarbonyl)phenylacetate

생성물 1

HCID 13575522(3S)-alpha-[[(2-Oxo-3-azetidinyl)amino]carbonyl]benzeneacetic acid, phenylmethyl ester

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6342Acetonitrile용매

반응 조건

온도
0 °C

실험 절차

The above azetidinone (3.0 g) is dissolved in 100 ml of dimethylformamide. The solution is cooled to 0° C. and 4.5 g of N-methylmorpholine is added followed (dropwise) by 10.8 g of α-(chlorocarbonyl)benzeneacetic acid, phenylmethyl ester in 50 ml of acetonitrile with stirring. The mixture is stirred for about 16 hours at 5° C. The solvent is distilled off in vacuo and 100 ml of water is added to the residue. The aqueous suspension is extracted twice with 100 ml portions of methylene chloride. The organic layers are combined, washed with sodium bicarbonate, 2N phosphoric acid and water, dried with sodium sulfate, filtered and evaporated to dryness. The residue is crystallized with ethyl acetate and petroleum ether, yielding 8.7 g, melting point 164°-166° C.

후처리

  1. stirringThe mixture is stirred for about 16 hours at 5° C
  2. distillationThe solvent is distilled off in vacuo and 100 ml of water
  3. additionis added to the residue
  4. extractionThe aqueous suspension is extracted twice with 100 ml portions of methylene chloride
  5. washwashed with sodium bicarbonate, 2N phosphoric acid and water
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe residue is crystallized with ethyl acetate and petroleum ether
  10. customyielding 8.7 g, melting point 164°-166° C.

출처 및 근거

ORD 기록
ord-97e3fa098dd74318b002fc9130922de1
출처 데이터셋
uspto-grants-1985_07
특허 번호
US04529698

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