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

HRID 533220Notes

Reaction equation

HRID 533220 reaction equation
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

Participants

5

Reactant 2

HCID 4378561Sodium methanethiolateHCID 59131551HCID 59131551, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-6862a19efb7f42d19e25a814c8957cc5
Source dataset
uspto-grants-2014_10
Patent number
US08853224B2

Reaction notes

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