Methanesulfonamide → HCID 178472579, compound

HRID 541109Notes

Reaction equation

HRID 541109 reaction equation
[OH:1][C@@H:2]([C@@H:7]([OH:19])[CH:8]1[CH2:10][N@@:9]1[C@@H:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:12])[C:3]([O:5][CH3:6])=[O:4].[CH3:20]S(N)(=O)=O>CC(O)(C)C.O>[OH:1][C@H:2]([C@@H:7]([OH:19])[CH:8]1[CH2:10][N@@:9]1[C@@H:11]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH3:12])[C:3]([O:5][CH2:6][CH3:20])=[O:4]

Participants

4

Reactant 2

HCID 72879MethanesulfonamideHCID 178501515HCID 178501515, compound

Product 1

HCID 178472579HCID 178472579, compound

Reagents, catalysts & solvents 1

HCID 714019492-Methylpropan-2-ol--water (1/1)Solvent

Procedure

To a solution of (2S,3S)-methyl 2,3-dihydroxy-3-((R)-1-((R)-1-phenylethyl)aziridin-2-yl)propanoate (3.3 g, 13.3 mmol) in t-BuOH/H2O (60 mL, 0.2 M/60 mL, 0.2 M) were added AD-mix α (33 g, 1000 w/w %) and methanesulfonamide (1.9 g, 19.9 mmol, 1.5 equiv) at 0° C. The reaction mixture was stirred for 24 hrs and quenched with water. The aqueous layer was extracted with ethyl acetate and the combined organic layer was washed with brine, dried over MgSO4, filtered through a pad of celite, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography with ethyl acetate/hexane (2/3) to afford the title product (diastereomeric mixture, ratio=7/1). Yield: 2.3 g (62%); yellow oil.

Workup

  1. customquenched with water
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washthe combined organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered through a pad of celite
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d2f6332038334e429910410a3e7f6fe4
Source dataset
uspto-grants-2014_10
Patent number
US08871950B1

Reaction notes

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