Ammonia → HCID 3380937, compound

HRID 1373738Notes

Reaction equation

HRID 1373738 reaction equation
C[O:2][C:3](=O)[CH:4]([NH:12][S:13]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH3:24]>CO>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([S:13]([NH:12][CH:4]([CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3]([NH2:24])=[O:2])(=[O:15])=[O:14])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 3330873HCID 3330873, compound

Product 1

HCID 3380937HCID 3380937, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To 2-(4-Chloro-benzenesulfonylamino)-3-phenyl-propionic acid methyl ester (750 mg) is added 10 mL of a 1.0 M solution of ammonia in methanol. The reaction is heated for 48 h at 65° C., cooled to room temperature, and the solvent removed. The resultant solid is first triturated with ethyl acetate, filtered, and then triturated with methylene chloride to provide the title compound. 1HNMR (400 MHz, CD3OD) 2.70 (dd, 1H, J=14.0 Hz and 9.6 Hz), 3.01 (dd, 1H, J=14.0 Hz and 5.4 Hz), 3.95 (dd, 1H, J=9.0 Hz and 5.0 Hz), 7.05–7.15 (m, 5H), 7.32–7.36 (m, 2H), and 7.53–7.56 (m, 2H). MS 339.1 m/z (M+1).

Workup

  1. temperaturecooled to room temperature
  2. customthe solvent removed
  3. customThe resultant solid is first triturated with ethyl acetate
  4. filtrationfiltered
  5. customtriturated with methylene chloride

Sources & evidence

ORD record
ord-6ad0d114696a46adb0739986296625a0
Source dataset
uspto-grants-2007_01
Patent number
US07163942B2

Reaction notes

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