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Hydrochloric Acid → (+/-)-13-Cyclohexyl-6,7-dihydro-6-hydroxymethyl-5H-indolo[2,1-a][2]benzazepine-10-carboxylic acid

HRID 1394883
ノート
印刷プレビュー

反応式

HRID 1394883 の反応式
[OH-].[Na+].[CH:3]1([C:9]2[C:10]3[CH:11]=[CH:12][C:13]([C:29]([O:31]C)=[O:30])=[CH:14][C:15]=3[N:16]3[CH2:22][CH:21]([CH2:23][OH:24])[CH2:20][C:19]4[CH:25]=[CH:26][CH:27]=[CH:28][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:29]([OH:31])=[O:30])=[CH:14][C:15]=3[N:16]3[CH2:22][CH:21]([CH2:23][OH:24])[CH2:20][C:19]4[CH:25]=[CH:26][CH:27]=[CH:28][C:18]=4[C:17]=23)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]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 14798Sodium HydroxideHCID 16072734methyl 13-cyclohexyl-6-(hydroxymethyl)-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylate

生成物 1

HCID 58765242(+/-)-13-Cyclohexyl-6,7-dihydro-6-hydroxymethyl-5H-indolo[2,1-a][2]benzazepine-10-carboxylic acid収率 69.4%

試薬・触媒・溶媒 2

HCID 887Methanol
溶媒
HCID 8028Tetrahydrofuran溶媒

反応条件

温度
100 °C

実験手順

Sodium hydroxide (0.2 mL of 1 N, 0.2 mmol) was added to a solution of methyl (±)-13-cyclohexyl-6,7-dihydro-6-hydroxymethyl-5H-indolo[2,1-a][2]benzazepine-10-carboxylate (15.0 mg, 0.037 mmol) in methanol (0.5 mL) and tetrahydrofuran (0.5 mL) in a microwave vial. The vial was sealed and the contents heated at 100° C. for 10 min in a microwave apparatus. The solution was acidified with dilute hydrochloric acid to precipitate the crude acid. The solid was collected and 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 (10.0 mg, 69%). ESI-MS m/z 390 (MH+); 1H NMR (500 MHz, MeOD) δ 1.19-1.34 (m, 1H) 1.36-1.56 (m, 2H) 1.63 (m, 1H) 1.74-1.87 (m, 2H) 1.91-2.21 (m, 5H) 2.37-2.60 (m, 1H) 2.74 (m, 1H) 2.97 (m, 1H) 3.36 (m, 1H) 3.47-3.67 (m, 2H) 4.59 (m, 1H) 7.38-7.50 (m, 4H) 7.72 (m, 1H) 7.88 (m, 1H) 8.18 (m, 1H).

後処理

  1. customThe vial was sealed
  2. customto precipitate the crude acid
  3. customThe solid was collected
  4. custompurified 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-cfc283661a344b579f2c4067a265bb78
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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