Hydrochloric Acid → 1-(Hydroxyphenylmethyl)cyclopropanesulfonamide

HRID 539596Notes

Reaction equation

HRID 539596 reaction equation
C(OC([NH:8][S:9]([C:12]1([CH:15]([OH:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:14][CH2:13]1)(=[O:11])=[O:10])=O)(C)(C)C.Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C>[OH:22][CH:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:12]1([S:9]([NH2:8])(=[O:10])=[O:11])[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 68353399N-tert-butyloxycarbonyl-1-(hydroxyphenylmethyl)cyclopropanesulfonamide

Product 1

HCID 682884261-(Hydroxyphenylmethyl)cyclopropanesulfonamideYield 99.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

880 mg of N-tert-butyloxycarbonyl-1-(hydroxyphenylmethyl)cyclopropanesulfonamide were dissolved in 25 ml of ethyl acetate, and 13.4 ml of a 1 N aqueous hydrochloric acid were added. The reaction solution was heated to 65° C. and the completeness of the conversion was checked with LCMS. After 8 hours, the mixture was neutralized with saturated aqueous sodium carbonate solution, and the organic phase was dried over Na2SO4 and concentrated by rotary evaporation. This gave the product (610 mg) with a molecular weight of 227.3 g/mol (C10H13NO3S); MS (ESI): m/e=210 (M−H2O+H+).

Workup

  1. dry with materialthe organic phase was dried over Na2SO4
  2. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-bb4d360b1faa43929e46c5cfcb4639ed
Source dataset
uspto-grants-2014_10
Patent number
US08871758B2

Reaction notes

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