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

HRID 713898노트

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HRID 713898 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  1. additionwas added
  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

출처 및 근거

ORD 기록
ord-9fe3b3ae0b65460fa33d1e6ca373b0b9
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09186367B2

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