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

HRID 2404084Notes

Reaction equation

HRID 2404084 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˜4.93 (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-d988ed1891914539a61742f3d44bac29
Source dataset
uspto-grants-2014_08
Patent number
US08802659B2

Reaction notes

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