Trifluoroacetic acid → 3-amino-N-(phenylsulfonyl)propanamide

HRID 713866Notes

Reaction equation

HRID 713866 reaction equation
[O:1]=[C:2]([NH:13][S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15])[CH2:3][CH2:4][NH:5]C(=O)OC(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[NH2:5][CH2:4][CH2:3][C:2]([NH:13][S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15])=[O:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66926414Tert-butyl 3-oxo-3-(phenylsulfonamido)propylcarbamate

Product 1

HCID 669264473-amino-N-(phenylsulfonyl)propanamideYield 40.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Tert-butyl 3-oxo-3-(phenylsulfonamido)propylcarbamate (3.6 g, 15.1 mmol) was dissolved in dichloromethane (60 mL). Then CF3COOH (1.1 mL, 0.3 mmol, 20 equiv) was added to the mixture at 0° C. and stirred for 2 h at 0° C. The reaction mixture was concentrated and purified by flash chromatograph to give 3-amino-N-(phenylsulfonyl)propanamide as a white solid (1.4 g, 40%). EDI-MS: 229.0 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ: 7.79˜7.71 (m, 2H), 7.70˜7.43 (brs, 3H), 7.42˜7.34 (m, 3H), 2.83 (t, 2H), 2.24 (t, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by flash chromatograph

Sources & evidence

ORD record
ord-15ece38449fc402393ac9928d77e756a
Source dataset
uspto-grants-2015_11
Patent number
US09186367B2

Reaction notes

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