1,8-Diazabicyclo(5.4.0)undec-7-ene → Ethyl 6,8-difluoro-1-methyl-4-oxo-7-((S)-3-trifluoroacetylamino-1-pyrrolidinyl)-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate

HRID 893577노트

반응식

HRID 893577 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:13])[C:11]=1F)[N:8]1[CH:14]([CH3:16])[S:15][C:7]1=[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:5]2=[O:22].Cl.[F:24][C:25]([F:35])([F:34])[C:26]([NH:28][C@H:29]1[CH2:33][CH2:32][NH:31][CH2:30]1)=[O:27].C1CCN2C(=NCCC2)CC1>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:13])[C:11]=1[N:31]1[CH2:32][CH2:33][C@H:29]([NH:28][C:26](=[O:27])[C:25]([F:35])([F:34])[F:24])[CH2:30]1)[N:8]1[CH:14]([CH3:16])[S:15][C:7]1=[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:5]2=[O:22]

참가 물질

5

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 9973824ethyl 6,7,8-trifluoro-1-methyl-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylateHCID 42614571(3S)-(-)-3-(Trifluoroacetamido)pyrrolidine Hydrochloride

생성물 1

HCID 54557724Ethyl 6,8-difluoro-1-methyl-4-oxo-7-((S)-3-trifluoroacetylamino-1-pyrrolidinyl)-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 1.34 g of ethyl 6,7,8-trifluoro-1-methyl-4-oxo-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate, 2.66 g of (S)-3-trifluoroacetylaminopyrrolidine hydrochloride [[α]D20 -28.6° (c=1, MeOH)], 1.80 g of 1.8-diazabicyclo[5,4,0]-7-undecene and 30 ml of N,N-dimethylformamide was stirred at room temperature for 5 hours. The reaction mixture was concentrated in vacuo, and water was added to the residue. The precipitate was collected by filtration and was chromatographed on silica gel using chloroform-methanol (8:2) to give the desired compound, which was recrystallized from methanol to give 0.80 g of pale yellow needles, m.p. 219°-224° C.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo, and water
  2. additionwas added to the residue
  3. filtrationThe precipitate was collected by filtration
  4. customwas chromatographed on silica gel

출처 및 근거

ORD 기록
ord-076e8384be844882a0cf22874991912a
출처 데이터셋
uspto-grants-1992_06
특허 번호
US05126337

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