2-Nitrobenzenesulfonyl chloride → methyl 2(S)-(tert-butoxycarbonylamino)-3-(2-nitrophenylsulfonamido)propanoate

HRID 1674545노트

반응식

HRID 1674545 반응식
[NH2:1][CH2:2][C@H:3]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:4]([O:6][CH3:7])=[O:5].CCN(C(C)C)C(C)C.[N+:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[S:34](Cl)(=[O:36])=[O:35])([O-:27])=[O:26]>C(Cl)Cl>[C:12]([O:11][C:9]([NH:8][C@@H:3]([CH2:2][NH:1][S:34]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[N+:25]([O-:27])=[O:26])(=[O:35])=[O:36])[C:4]([O:6][CH3:7])=[O:5])=[O:10])([CH3:15])([CH3:14])[CH3:13]

참가 물질

5

반응물 3

HCID 155402-Nitrobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 11746086(S)-Methyl 3-amino-2-((tert-butoxycarbonyl)amino)propanoate

생성물 1

HCID 58798583methyl 2(S)-(tert-butoxycarbonylamino)-3-(2-nitrophenylsulfonamido)propanoate수율 98.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a mixture of methyl 3-amino-2(S)-(tert-butoxycarbonylamino)propanoate ii (1.6 g, 7.3 mmol.) in DCM (50 mL) was added DIPEA (1.64 mL, 9.4 mmol.) and 2-nitrobenzene sulfonyl chloride (1.62 g, 7.3 mmol.). The mixture was stirred at rt for 2 h. It was then concentrated, dissolved in ethyl acetate, which was then washed with sat. sodium bicarbonate, brine and dried over magnesium sulfate. It was then filtered, concentrated to yield 2.9 g (98%) of methyl 2(S)-(tert-butoxycarbonylamino)-3-(2-nitrophenylsulfonamido)propanoate iii as a yellow foam. 1H NMR (CD3OD, 300 MHz) δ 1.41 (s, 9H), 3.36-3.51 (m, 2H), 3.71 (s, 3H), 4.22 (m, 1H), 7.80-7.90 (m, 3H), 8.07-8.10 (m, 1H).

후처리

  1. concentrationIt was then concentrated
  2. dissolutiondissolved in ethyl acetate
  3. washwhich was then washed with sat. sodium bicarbonate, brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationIt was then filtered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4e31f78f246c40f1b3872760ed0e8c25
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003604B2

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