Sodium Hydroxide → HCID 67237069, compound

HRID 1748281Notes

Reaction equation

HRID 1748281 reaction equation
[CH3:1][C@@H:2]1[N:8]2[C:9]3[CH:10]=[C:11]([C:16]([O:18]CC)=[O:17])[CH:12]=[CH:13][C:14]=3[CH:15]=[C:7]2[C:6](=[O:21])[NH:5][CH2:4][CH2:3]1.[OH-].[Na+]>C(O)C>[CH3:1][C@@H:2]1[N:8]2[C:9]3[CH:10]=[C:11]([C:16]([OH:18])=[O:17])[CH:12]=[CH:13][C:14]=3[CH:15]=[C:7]2[C:6](=[O:21])[NH:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67234992HCID 67234992, compound

Product 1

HCID 67237069HCID 67237069, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl (5S)-5-methyl-1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylate (1.9 g, 6.7 mmol) in ethanol (75 mL) is added 1N NaOH solution (16 mL, 16 mmol). The reaction mixture is refluxed for 1.5 h and cooled to room temperature. The ethanol is removed under vacuum and the residue is diluted with water. The mixture is acidified with aqueous 1N HCl solution the resulting solid is collected by filtration, rinsed with water and dried to afford the title compound (1.7 g, 99%).

Workup

  1. temperatureThe reaction mixture is refluxed for 1.5 h
  2. customThe ethanol is removed under vacuum
  3. additionthe residue is diluted with water
  4. filtrationis collected by filtration
  5. washrinsed with water
  6. customdried

Sources & evidence

ORD record
ord-774ae0830a574ceb8d181250f9a8353a
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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