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Hydrochloric Acid → Methyl (+/-)-13-cyclohexyl-6,7-dihydro-6-carboxy-6-methyl-5H-indolo[2,1-a][2]benzazepine-10-carboxylate

HRID 1394900
ノート
印刷プレビュー

反応式

HRID 1394900 の反応式
[OH-].[Li+].[CH:3]1([C:9]2[C:10]3[CH:11]=[CH:12][C:13]([C:32]([O:34][CH3:35])=[O:33])=[CH:14][C:15]=3[N:16]3[CH2:22][C:21]([C:24]([O:26]C)=[O:25])([CH3:23])[CH2:20][C:19]4[CH:28]=[CH:29][CH:30]=[CH:31][C:18]=4[C:17]=23)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.Cl>CO.O1CCCC1>[CH:3]1([C:9]2[C:10]3[CH:11]=[CH:12][C:13]([C:32]([O:34][CH3:35])=[O:33])=[CH:14][C:15]=3[N:16]3[CH2:22][C:21]([C:24]([OH:26])=[O:25])([CH3:23])[CH2:20][C:19]4[CH:28]=[CH:29][CH:30]=[CH:31][C:18]=4[C:17]=23)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58677045Methyl (+/-)-13-cyclohexyl-6,7-dihydro-6-carbomethoxy-6-methyl-5H-indolo[2,1-a][2]benzazepine-10-carboxylate

生成物 1

HCID 58677019Methyl (+/-)-13-cyclohexyl-6,7-dihydro-6-carboxy-6-methyl-5H-indolo[2,1-a][2]benzazepine-10-carboxylate収率 34%

試薬・触媒・溶媒 2

HCID 887
Methanol
溶媒
HCID 8028Tetrahydrofuran溶媒

反応条件

温度
65 °C

実験手順

Lithium hydroxide (12 mg, 0.5 mmol) was added to a solution of methyl (±)-13-cyclohexyl-6,7-dihydro-6-carbomethoxy-6-methyl-5H-indolo[2,1-a][2]benzazepine-10-carboxylate (20.0 mg, 0.045 mmol) in methanol (1.0 mL) and tetrahydrofuran (1.0 mL) in a microwave vial. The vial was sealed and the contents heated at 65° C. for 50 min in a microwave apparatus. The solution was acidified with dilute hydrochloric acid to precipitate the crude acid. The solid was collected and was purified on the Shimadzu preparative liquid chromatograph. The product containing fraction was concentrated on a Speed Vac® to leave the titled compound as a white solid (6.5 mg, 34%). ESI-MS m/z 432 (MH+) 1H NMR (500 MHz, CHLOROFORM-D) δ ppm 1.18-1.51 (m, 6 H) 1.62-1.83 (m, 3 H) 1.89-2.14 (m, 4 H) 2.36 (d, J=13.73 Hz, 0.5 H) 2.72 (d, J=13.43 Hz, 0.5 H) 2.89-2.98 (m, 1 H) 3.01 (d, J=13.73 Hz, 0.5 H) 3.19 (d, J=14.04 Hz, 0.5 H) 3.32 (d, J=14.65 Hz, 0.5 H) 3.90 (d, J=14.60 Hz, 0.5 H) 3.94 (d, J=17.70 Hz, 3 H) 4.31 (d, J=14.65 Hz, 0.5 H) 4.89 (d, J=14.65 Hz, 0.5 H) 7.30-7.50 (m, 4 H) 7.75 (dd, J=23.04, 8.39 Hz, 1H) 7.86 (dd, J=24.87, 8.39 Hz, 1 H) 8.11 (s, 0.5 H) 8.28 (s, 0.5 H).

後処理

  1. customThe vial was sealed
  2. customto precipitate the crude acid
  3. customThe solid was collected
  4. customwas purified on the Shimadzu preparative liquid chromatograph
  5. additionThe product containing fraction
  6. concentrationwas concentrated on a Speed Vac®

出典と根拠

ORDレコード
ord-7225c71e28714cb18f21adcf56c92a66
出典データセット
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07348425B2

反応ノート

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