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

HRID 1394902
Notes
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Reaction equation

HRID 1394902 reaction equation
[OH-].[Na+].[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])([F: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])([F:23])[CH2:20][C:19]4[CH:28]=[CH:29][CH:30]=[CH:31][C:18]=4[C:17]=23)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58677086methyl (+/-)-13-cyclohexyl-6,7-dihydro-6-carbomethoxy-6-fluoro-5H-indolo[2,1-a][2]benzazepine-10-carboxylate

Product 1

HCID 58677052Methyl (+/-)-13-cyclohexyl-6,7-dihydro-6-carboxy-6-fluoro-5H-indolo[2,1-a][2]benzazepine-10-carboxylateYield 85%

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

Sodium hydroxide (50 μL of 1N, 0.05 mmol) was added to a solution of methyl (±)-13-cyclohexyl-6,7-dihydro-6-carbomethoxy-6-fluoro-5H-indolo[2,1-a][2]benzazepine-10-carboxylate (12.0 mg, 0.027 mmol) in methanol (0.5 mL) and tetrahydrofuran (0.5 mL) in a microwave vial. The vial was sealed and the contents heated at 65° C. for 20 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 (10 mg, 85%). ESI-MS m/z 436 (MH+).

Workup

  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®

Sources & evidence

ORD record
ord-9643b30bca92480f99c43d63d57220b1
Source dataset
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07348425B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes