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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
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HRID 1394900 반응식
[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
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참가 물질

6

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

생성물 1

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

시약·촉매·용매 2

HCID 887
Methanol
용매
HCID 8028Tetrahydrofuran용매

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온도
65 °C

실험 절차

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).

후처리

  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®

출처 및 근거

ORD 기록
ord-7225c71e28714cb18f21adcf56c92a66
출처 데이터셋
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07348425B2

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