Hydrochloric Acid → HCID 69367839, compound

HRID 6953Notes

Reaction equation

HRID 6953 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[C:12]([O:17][CH2:18][CH2:19][N:20](C(OC(C)(C)C)=O)[CH3:21])[CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[S:29]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=[O:31])=[O:30])=O)(C)(C)C.[ClH:38]>CCO>[ClH:38].[C:32]1([S:29]([C:9]2[NH:8][C:16]3[C:11]([CH:10]=2)=[C:12]([O:17][CH2:18][CH2:19][NH:20][CH3:21])[CH:13]=[CH:14][CH:15]=3)(=[O:31])=[O:30])[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 235446272-Benzenesulfonyl-4-[2-(tert-butoxycarbonyl-methyl-amino)-ethoxy]-indole-1-carboxylic acid tert-butyl ester

Product 1

HCID 69367839HCID 69367839, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

2-Benzenesulfonyl-4-[2-(tert-butoxycarbonyl-methyl-amino)-ethoxy]-indole-1-carboxylic acid tert-butyl ester (0.250 g., 0.5 mmol) from Step 3 was dissolved in 5 mL EtOH. To this solution was added 1 mL of 2M ethanolic hydrogen chloride solution. The reaction mixture was heated at 100° C. for 35 minutes. Upon cooling to ambient temperature, a fine white precipitate was observed. After filtration and drying in vacuo at 60° C., [2-(2-benzenesulfonyl-1H-indol-4-yloxy)-ethyl]-methyl-amine hydrochloride was obtained. MS: 330 (M+H)+, mp=250.7–252.1° C.

Workup

  1. temperatureUpon cooling to ambient temperature
  2. filtrationAfter filtration
  3. customdrying in vacuo at 60° C.

Sources & evidence

ORD record
ord-0598c4a6efe64da582219cf0fd57ed5b
Source dataset
uspto-grants-2006_08
Patent number
US07084169B2

Reaction notes

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