Acetic Acid → HCID 66641242, compound

HRID 37974Notes

Reaction equation

HRID 37974 reaction equation
C([O:3][C:4]([CH:6]1[C:12]2[NH:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[C:11]=2[CH2:10][CH2:9][N:8]([C:20](=[O:28])[C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[CH2:7]1)=[O:5])C.[OH-].[Na+].CC(O)=O>O1CCOCC1.O>[F:27][C:24]1[CH:23]=[CH:22][C:21]([C:20]([N:8]2[CH2:9][CH2:10][C:11]3[C:19]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[NH:13][C:12]=3[CH:6]([C:4]([OH:5])=[O:3])[CH2:7]2)=[O:28])=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 666401053-(4-Fluorobenzoyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole-5-carboxylic acid ethyl ester

Product 1

HCID 66641242HCID 66641242, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 3-(4-fluorobenzoyl)-1,2,3,4,5,6-hexahydro-azepino[4,5-b]indole-5-carboxylic acid ethyl ester (543 mg, 1.42 mmol) in 1,4-dioxane (8 mL) was added aqueous sodium hydroxide (114 mg in 2 mL Of water). The mixture was stirred for 1 hour at 20° C. Solvent was then removed under high vacuum to give a crude product, which was redissolved in water and acidified with AcOH. Solid was collected by filtration and washed with water and dried under high vacuum to give 3-(4-fluorobenzoyl)-1,2,3,4,5,6-hexahydro-azepino[4,5-b]indole-5-carboxylic acid (421 mg, 84%); MS (ES): 353 (MH+).

Workup

  1. customSolvent was then removed under high vacuum
  2. customto give a crude product, which
  3. filtrationSolid was collected by filtration
  4. washwashed with water
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-d292c0790deb477a959af2eb2ba28b4e
Source dataset
uspto-grants-2013_09
Patent number
US08524704B2

Reaction notes

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