Anzemet → methanesulfonic acid;(10-oxo-8-azatricyclo[5.3.1.03,8]undecan-5-yl) 1H-indole-3-carboxylate;hydrate

HRID 20205Notes

Reaction equation

HRID 20205 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[O:6]=[C:7]1[CH:16]2[CH2:17][CH:10]3[CH2:11][CH:12]([O:18][C:19]([C:21]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[NH:23][CH:22]=4)=[O:20])[CH2:13][CH:14]([CH2:15]2)[N:9]3[CH2:8]1>CC(C)=O>[OH2:3].[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[O:6]=[C:7]1[CH:16]2[CH2:17][CH:10]3[CH2:11][CH:12]([O:18][C:19]([C:21]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[NH:23][CH:22]=4)=[O:20])[CH2:13][CH:14]([CH2:15]2)[N:9]3[CH2:8]1

Participants

4

Reactant 2

HCID 3148AnzemetHCID 6395Methanesulfonic Acid

Product 1

HCID 22058225methanesulfonic acid;(10-oxo-8-azatricyclo[5.3.1.03,8]undecan-5-yl) 1H-indole-3-carboxylate;hydrateYield 148.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
25 °C

Procedure

Methanesulphonic acid (0.34 mL, 5.24 mmol) is added to a solution of 1H-Indole-3-carboxylic acid 10-oxo-8-aza-tricyclo[5.3.1.03,8]undec-5-yl ester (1.6 gr, 4.93 mmol) in acetone (20 mL) and under nitrogen, maintaining the reaction temperature around 25° C. Following stirring at 0° C. for 3 h, and at room temperature for one night, the solid that forms is filtered and washed with acetone. The product formed is recrystallised from isopropanol-water (95:5 by weight), to obtain 1H-Indole-3-carboxylic acid 10-oxo-8-aza-tricyclo[5.3.1.03,8]undec-5-yl ester methanesulphonate monohydrate (1.71 gr, 79%) in the form of a white solid.

Workup

  1. waitat room temperature for one night
  2. filtrationthe solid that forms is filtered
  3. washwashed with acetone
  4. customThe product formed
  5. customis recrystallised from isopropanol-water (95:5 by weight)

Sources & evidence

ORD record
ord-7be6600dba3e4bbd9e8aa81eb57a4489
Source dataset
uspto-grants-2010_06
Patent number
US07745628B2

Reaction notes

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