Sodium methanethiolate → benzyl (R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(methylthio)ethylcarbamate

HRID 533220노트

반응식

HRID 533220 반응식
CS(O[CH2:6][C@H:7]([NH:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[C@@H:8]1[CH2:12][O:11][C:10]([CH3:14])([CH3:13])[O:9]1)(=O)=O.[CH3:26][S-:27].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH3:14][C:10]1([CH3:13])[O:9][C@H:8]([C@@H:7]([NH:15][C:16](=[O:17])[O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:6][S:27][CH3:26])[CH2:12][O:11]1

참가 물질

5

반응물 2

HCID 4378561Sodium methanethiolateHCID 59131551HCID 59131551, 화합물

생성물 1

HCID 58287015benzyl (R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(methylthio)ethylcarbamate수율 89.3%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of the product from Example 27.2 (2.58 g, 6.91 mmol) in dimethylformamide (10 ml) was added sodium thiomethoxide (0.630 g, 8.98 mmol). The reaction mixture was stirred at ambient temperature for 16 h. The reaction mixture was diluted with ethyl acetate and washed with water (4×), dried (MgSO4) and evaporated. The residue was chromatographed on silica gel (ethyl acetate-petrol, 1:4) giving a colourless oil (2.007 g, 89%). 1H NMR (CDCl3) δ 7.35 (m, 5H), 5.12 (ABq, 2H), 5.07 (br. s, 1H), 4.47 (bit, J=7.2 Hz, 1H), 4.05 (t, J=7.2 Hz, 1H), 3.83 (brq, J=7.2 Hz, 1H), 3.70 (dd, J=8.3, 6.8 Hz, 1H), 2.69 (d, J=7.6 Hz, 2H), 2.15 (s, 3H), 1.42 (s, 3H), 1.34 (s, 3H).

후처리

  1. washwashed with water (4×)
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue was chromatographed on silica gel (ethyl acetate-petrol, 1:4)

출처 및 근거

ORD 기록
ord-6862a19efb7f42d19e25a814c8957cc5
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853224B2

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