Hydrochloric Acid → Methyl 4-(2-aminoethylsulfonyl)benzoate hydrochloride

HRID 2111155Notes

Reaction equation

HRID 2111155 reaction equation
C(OC([NH:8][CH2:9][CH2:10][S:11]([C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=1)(=[O:13])=[O:12])=O)(C)(C)C.[ClH:24].CCOCC>ClCCl.O1CCOCC1>[ClH:24].[NH2:8][CH2:9][CH2:10][S:11]([C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=1)(=[O:13])=[O:12]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 66688741HCID 66688741, compound

Product 1

HCID 66688214Methyl 4-(2-aminoethylsulfonyl)benzoate hydrochloride

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl 4-(2-tert-butoxycarbonylaminoethanesulfonyl)benzoate (2.86 g, 8.33 mmol) in dichloromethane (20 ml) was treated with 4M HCl in dioxane (20 ml) for 2 h. Ether (200 ml) was added and the suspension was filtered, washed with ether (2×50 ml), hexane (50 ml) and pumped dry to give methyl 4-(2-aminoethylsulfonyl)benzoate hydrochloride (2.23 g) which was coupled with benzofuran 2-carboxylic acid as described above to afford the title compound. MS (M+1): 388.

Workup

  1. filtrationthe suspension was filtered
  2. washwashed with ether (2×50 ml), hexane (50 ml)
  3. custompumped dry

Sources & evidence

ORD record
ord-4b2d246dc0a147b49644102ef23126f1
Source dataset
uspto-grants-2009_04
Patent number
US07517988B2

Reaction notes

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