benzyl (R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(methylthio)ethylcarbamate → HCID 58287045, compound

HRID 533221Notes

Reaction equation

HRID 533221 reaction equation
[CH3:1][C:2]1([CH3:22])[O:6][C@H:5]([C@@H:7]([NH:11]C(=O)OCC2C=CC=CC=2)[CH2:8][S:9][CH3:10])[CH2:4][O:3]1>C(O)(C)C.[OH-].[K+]>[CH3:1][C:2]1([CH3:22])[O:6][C@H:5]([C@@H:7]([NH2:11])[CH2:8][S:9][CH3:10])[CH2:4][O:3]1

Participants

4

Reactant 1

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

Product 1

HCID 58287045HCID 58287045, compoundYield 77.4%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

A stirred solution of the product from Example 27.3 (2.007 g, 6.17 mmol) in isopropanol (34 ml) and 2M potassium hydroxide (15 ml) was heated at 80° C. for 64 h. The reaction mixture was concentrated to remove isopropanol. The residue was diluted with water and extracted with diethyl ether (3×), dried (MgSO4) and evaporated. The residue was chromatographed on silica gel (ethyl acetate-petrol, 2:1 then methanol-ethyl acetate, 2:98) giving a pale yellow oil (0.913 g, 77%). 1H NMR (CDCl3) δ 4.06 (m, 2H), 3.79 (m, 1H), 2.90 (m, 1H), 2.61 (dd, J=13.2, 4.5 Hz, 1H), 2.44 (dd, J=13.2, 8.7 Hz, 1H), 2.12 (s, 3H), 1.43 (s, 3H), 1.36 (s, 3H). 13C NMR (CDCl3) δ 109.5, 79.0, 66.9, 52.7, 39.9, 26.9, 25.6, 16.3, 14.6.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto remove isopropanol
  3. additionThe residue was diluted with water
  4. extractionextracted with diethyl ether (3×)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was chromatographed on silica gel (ethyl acetate-petrol, 2:1

Sources & evidence

ORD record
ord-55fbf65fd87548fba6d178c353787b2d
Source dataset
uspto-grants-2014_10
Patent number
US08853224B2

Reaction notes

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