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

HRID 713899Notes

Reaction equation

HRID 713899 reaction equation
[CH3:1][S:2]([NH:5][C:6](=[O:17])[CH2:7][CH2:8][NH:9]C(=O)OC(C)(C)C)(=[O:4])=[O:3].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:9][CH2:8][CH2:7][C:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[O:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86668418Tert-butyl 3-(methylsulfonamido)-3-oxopropylcarbamate

Product 1

HCID 140282353-amino-N-(methylsulfonyl)propanamideYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

tert-butyl 3-(methylsulfonamido)-3-oxopropylcarbamate (3.6 g, 15.1 mmol) was dissolved in DCM (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. The residue was purified by flash chromatography to give 3-amino-N-(methylsulfonyl)propanamide as a transparent solid (1.8 g, 80%), (mobile phase: CH3OH/H2O=0˜5%). ESI-MS (M+1)+: 167.0. 1H NMR (400 MHz, CD3OD) δ: 3.21˜3.11 (m, 2H), 3.07 (s, 3H), 2.60˜2.54 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-fca08ac47c7c488f877f357dfc8e259f
Source dataset
uspto-grants-2015_11
Patent number
US09186367B2

Reaction notes

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