2,6-Lutidine → (4-Pyridylthiomethyl]-7-[(2,5-dichlorophenyl)-thioacetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 1378686

反応式

HRID 1378686 の反応式
IC[C:3]1[CH2:10][S:9][C@H:8]2[N:5]([C:6](=[O:23])[C@H:7]2[NH:11][C:12](=[S:22])[CH2:13][C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=2[Cl:21])[C:4]=1[C:24]([O-:26])=[O:25].[SH:27][C:28]1[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=1.N1C(C)=CC=C[C:35]=1C>C1COCC1.C(OCC)(=O)C>[N:31]1[CH:32]=[CH:33][C:28]([S:27][CH2:35][O:26][C:24]([C:4]2[N:5]3[CH:8]([S:9][CH2:10][CH:3]=2)[CH:7]([NH:11][C:12](=[S:22])[CH2:13][C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=2[Cl:21])[C:6]3=[O:23])=[O:25])=[CH:29][CH:30]=1

参加物

6

反応物 3

HCID 79372,6-LutidineHCID 86749943(6R)-trans-3-Iodomethyl-7-[(2,5-dichlorophenyl)thioacetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateHCID 178418431pyridine-4-thiol

生成物 1

HCID 86749942(4-Pyridylthiomethyl]-7-[(2,5-dichlorophenyl)-thioacetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

(6R)-trans-3-Iodomethyl-7-[(2,5-dichlorophenyl)thioacetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate, diphenylmethyl ester (3.00 g, 4.14 mmol) was dissolved in THF (50 mL) at 0° C. and treated with 4-mercaptopyridine (0.504 g, 4.54 mmol). A solution of 2,6-lutidine (0.576 g, 5.38 mmol) in THF (1 mL) was added next, and the reaction mixture was stirred at 0° C. for 0.5 h and then at 20° C. for 1 h. The mixture was diluted with ethyl acetate (500 mL) and the organic solution was washed with water (2×500 mL) and brine (100 mL). The solution was then dried (MgSO4) and evaporated under reduced pressure to give an oil which was treated with Et20 (50 mL) to give a solid. The solid was collected by filtration and purified by column chromatography on silica gel (CH2Cl2 to 30% EtOAc/CH2Cl2) to give 1.50 g of (6R)-trans-3-[(4-pyridylthiomethyl]-7-[(2,5-dichlorophenyl)thioacetamido]-8-oxo-5-thia-1-azabicyclo [4.2.0]oct-2-ene-2-carboxylate, diphenylmethyl ester as a tan solid (49% yield), m.p. 122° C. 1H NMR (300 MHz, CDCl3) δ 3.37 (d, J=18 Hz, 1 H), 3.52 (d, J=18 Hz, 1 H), 3.68 (d, J=17 Hz, 1 H), 3.76 (d, J=17 Hz, 1 H), 3.96 (d, J=13 Hz, 1 H), 4.16 (d, J=13 Hz, 1 H), 4.93 (d, J=5 Hz, 1 H), 5.76 (dd, J=5, 9 Hz, 1 H), 6.95-7.42 (m, 16 H), 7.49 (d, J=9 Hz, 1 H), 8.29 (d, J=6 Hz, 2 H). Anal. Calcd. for C34H27N3O4S3Cl2 : C, 57.62; H, 3.84; N, 5.93. Found: C, 57.27; H, 3.68; N, 5.79.

後処理

  1. waitat 20° C. for 1 h
  2. washthe organic solution was washed with water (2×500 mL) and brine (100 mL)
  3. dry with materialThe solution was then dried (MgSO4)
  4. customevaporated under reduced pressure
  5. customto give an oil which
  6. additionwas treated with Et20 (50 mL)
  7. customto give a solid
  8. filtrationThe solid was collected by filtration
  9. custompurified by column chromatography on silica gel (CH2Cl2 to 30% EtOAc/CH2Cl2)

出典と根拠

ORDレコード
ord-4044f3d215284fa7972a4dc47e5517b6
出典データセット
uspto-grants-1997_09
特許番号
US05668284

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