Hydrochloric Acid → HCID 23152496, compound

HRID 1012300Notes

Reaction equation

HRID 1012300 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:26]=[CH:25][C:24]([C:27]([NH:29][C:30]4([C:34]([NH:36][C:37]5[CH:42]=[CH:41][C:40](/[CH:43]=[CH:44]/[C:45]([O:47]CC)=[O:46])=[CH:39][CH:38]=5)=[O:35])[CH2:33][CH2:32][CH2:31]4)=[O:28])=[CH:23][C:9]=3[N:10]3[C:16]=2[C:15]2[CH:17]=[CH:18][C:19]([O:21][CH3:22])=[CH:20][C:14]=2[O:13][CH2:12][CH2:11]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].Cl>O1CCCC1.CO>[CH:1]1([C:7]2[C:8]3[CH:26]=[CH:25][C:24]([C:27]([NH:29][C:30]4([C:34]([NH:36][C:37]5[CH:42]=[CH:41][C:40](/[CH:43]=[CH:44]/[C:45]([OH:47])=[O:46])=[CH:39][CH:38]=5)=[O:35])[CH2:31][CH2:32][CH2:33]4)=[O:28])=[CH:23][C:9]=3[N:10]3[C:16]=2[C:15]2[CH:17]=[CH:18][C:19]([O:21][CH3:22])=[CH:20][C:14]=2[O:13][CH2:12][CH2:11]3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58826664HCID 58826664, compound

Product 1

HCID 23152496HCID 23152496, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl (E)-3-[4-({1-[(12-cyclohexyl-3-methoxy-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carbonyl)amino]cyclobutanecarbonyl}amino)phenyl]acrylate (102 mg, 0.154 mmol) in tetrahydrofuran (3 ml) and methanol (2 ml), was added 2N aqueous sodium hydroxide solution (1.2 ml), and the mixture was stirred at room temperature for 17 hr. 2N Hydrochloric acid (1.3 ml) was added and the mixture was extracted with ethyl acetat. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. Hexane:diethyl ether (1:1) solution was added to the obtained residue, and the precipitated solid was collected by filtration and washed with hexane:diethyl ether (1:1) solution. The obtained solid was dried in vacuo to give (E)-3-[4-({1-[(12-cyclohexyl-3-methoxy-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carbonyl)amino]cyclobutanecarbonyl}amino)phenyl]acrylic acid (84 mg, yield 86%).

Workup

  1. extractionthe mixture was extracted with ethyl acetat
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated under reduced pressure
  6. additionHexane:diethyl ether (1:1) solution was added to the obtained residue
  7. filtrationthe precipitated solid was collected by filtration
  8. washwashed with hexane:diethyl ether (1:1) solution
  9. customThe obtained solid was dried in vacuo

Sources & evidence

ORD record
ord-ab092f2a808d45d9a7442554ef847c39
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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