Trifluoroacetic acid → (6R)-trans-3-chloromethyl-7-[(2,5-dichlorophenyl)thioacetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 53610ノート

反応式

HRID 53610 の反応式
C1(C([O:14][C:15]([C:17]2[N:18]3[C@H:21]([S:22][CH2:23][C:24]=2[CH2:25][Cl:26])[C@H:20]([NH:27][C:28](=[S:38])[CH2:29][C:30]2[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:31]=2[Cl:37])[C:19]3=[O:39])=[O:16])C2C=CC=CC=2)C=CC=CC=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:26][CH2:25][C:24]1[CH2:23][S:22][C@H:21]2[N:18]([C:19](=[O:39])[C@H:20]2[NH:27][C:28](=[S:38])[CH2:29][C:30]2[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:31]=2[Cl:37])[C:17]=1[C:15]([OH:16])=[O:14]

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 22871934(6R)-trans-3-chloromethyl-7-[(2,5-dichlorophenyl)thioacetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate diphenylmethyl ester

生成物 1

HCID 21969808(6R)-trans-3-chloromethyl-7-[(2,5-dichlorophenyl)thioacetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid収率 72.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

A slurry of (6R)-trans-3-chloromethyl-7-[(2,5-dichlorophenyl)thioacetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate diphenylmethyl ester (10.0 g, 15.8 mmol) in CH2Cl2 (200 mL) at 0° C. was treated with anisole (24 mL) and then trifluoroacetic acid (80 mL). The resulting solution was stirred for 1 h at 0° C. and then concentrated under reduced pressure. The residue was stirred with Et2O, and the resulting solid was collected by filtration to give 5.20 g of (6R)-trans-3-chloromethyl-7-[(2,5-dichlorophenyl)-thioacetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid as a white solid (70% yield), m.p. 125° C. 1H NMR (300 MHz, DMSO-d6) δ3.51 (d, J=18 Hz, 1H), 3.70 (d, J=18 Hz, 1H), 3.91 (s, 2H), 4.52 (d, J=11 Hz, 1H), 4.58 (d, J=11 Hz, 1H), 5.13 (d, J=5 Hz, 1H), 5.70 (dd, J=5, 8 Hz, 1H), 7.24 (dd, J=2, 8 Hz, 1H), 7.47 (dd, J=2, 8 Hz, 2H), 9.28 (d, J=8 Hz, 1H).

後処理

  1. concentrationconcentrated under reduced pressure
  2. stirringThe residue was stirred with Et2O
  3. filtrationthe resulting solid was collected by filtration

出典と根拠

ORDレコード
ord-26e02884ae3a46a8aebbb1e7daf48c61
出典データセット
uspto-grants-1997_04
特許番号
US05620969

反応ノート

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