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 893577ノート

反応式

HRID 893577 の反応式
[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]

参加物

5

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-076e8384be844882a0cf22874991912a
出典データセット
uspto-grants-1992_06
特許番号
US05126337

反応ノート

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