1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Tert-butyl 3-(methylsulfonamido)-3-oxopropylcarbamate

HRID 2404118Notes

Reaction equation

HRID 2404118 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].[CH3:14][S:15]([NH2:18])(=[O:17])=[O:16].CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:14][S:15]([NH:18][C:11](=[O:13])[CH2:10][CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:17])=[O:16]

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 72879MethanesulfonamideHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanine

Product 1

HCID 86668418Tert-butyl 3-(methylsulfonamido)-3-oxopropylcarbamateYield 90%

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 methanesulfonamide (1.43 g, 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 r.t. 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 DCM. The combined organic layer was washed by 5% HCl, brine, dried over Na2SO4, concentrated to give tert-butyl 3-(methylsulfonamido)-3-oxopropylcarbamate as a gray oil (3.6 g, 90%). ESI-MS (M+H)+: 267.1. 1H NMR (400 MHz, DMSO-d6) δ: 6.91˜6.83 (brs, 1H), 3.36 (s, 3H), 3.19˜3.12 (m, 2H), 2.41 (t, 2H), 1.37 (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 DCM
  5. washThe combined organic layer was washed by 5% HCl, brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e9613871c2344da2ae500103730ff1c7
Source dataset
uspto-grants-2014_08
Patent number
US08802659B2

Reaction notes

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