Benzenesulfonamide → Tert-butyl 3-oxo-3-(phenylsulfonamido)propylcarbamate

HRID 713865Notes

Reaction equation

HRID 713865 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:14]1([S:20]([NH2:23])(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[O:13]=[C:11]([NH:23][S:20]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:22])=[O:21])[CH2:10][CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 7370BenzenesulfonamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanine

Product 1

HCID 66926414Tert-butyl 3-oxo-3-(phenylsulfonamido)propylcarbamateYield 106.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

3-(Tert-butoxycarbonylamino)propanoic acid (4 g, 21.2 mmol, 1.0 equiv) was dissolved in DCM (100 mL). Then phenylsulfonamide (15.1 mmol, 0.7 equiv), EDCI (3.45 g, 18.2 mmol, 0.85 equiv) and DMAP (0.37 g, 3 mmol, 0.15 equiv) were added to the mixture and stirred for 2 h at room temperature. The reaction mixture was cooled down to 0° C., ice water (100 mL) was added. The mixture was stirred for 15 min, separated and the water layer was extracted twice with dichloromethane. The combined organic layer was washed by 5% HCl, brine, dried over Na2SO4, concentrated to give tert-butyl 3-oxo-3-(phenylsulfonamido)propylcarbamate 5.3 g, gray oil, 100%. EDI-MS: 329.0 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 9.52˜9.43 (brs, 1H), 8.02˜7.96 (m, 2H), 7.61˜7.55 (m, 1H), 7.50˜7.45 (m, 2H), 5.02˜4.23 (m, 1H), 3.30˜3.24 (m, 2H), 2.48˜2.41 (m, 2H), 1.34 (s, 9H).

Workup

  1. temperatureThe reaction mixture was cooled down to 0° C.
  2. stirringThe mixture was stirred for 15 min
  3. customseparated
  4. extractionthe water layer was extracted twice with dichloromethane
  5. washThe combined organic layer was washed by 5% HCl, brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1fe5f6d350ca41a49155febe2374f00a
Source dataset
uspto-grants-2015_11
Patent number
US09186367B2

Reaction notes

Loading…