Methanesulfonyl chloride → HCID 86678015, compound

HRID 246760Notes

Reaction equation

HRID 246760 reaction equation
[OH:1][CH:2]1[CH2:7][O:6][CH2:5][CH:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:3]1.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>CN(C)C1C=CN=CC=1.ClCCl>[CH3:16][S:17]([O:1][CH:2]1[CH2:3][CH:4]([NH:8][C:9]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:15])[CH2:5][O:6][CH2:7]1)(=[O:19])=[O:18]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 712801951,5-Anhydro-2,3-dideoxy-2-[[(1,1-dimethylethoxy)carbonyl]amino]pentitol

Product 1

HCID 86678015HCID 86678015, compoundYield 67.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 5-hydroxy-tetrahydro-2H-pyran-3-ylcarbamate (109 mg, 0.5 mmol) and N,N-dimethylpyridin-4-amine (80 mg, 0.65 mmol) in 10 mL of dichloromethane was cooled in an ice bath, methanesulfonyl chloride (0.05 mL, 0.6 mmol) was added drop-wise. The reaction mixture was stirred overnight at room temperature, then was washed with 50 mL of water, organic phase dried with sodium sulfate filtered and concentrated. The residue was purified by column chromatography (silica gel. 200-300 mesh, eluting with ethyl acetate/petroleum ether=1/1) to afford 5-(tert-butoxycarbonylamino)-tetrahydro-2H-pyran-3-yl methanesulfonate (100 mg, 67%) as white solid. LCMS: (M+H)+=318; 1H NMR (300 MHz, CDCl3): δ 4.89-4.83 (m, 1H), 3.99-3.62 (m, 5H), 3.06 (s, 3H), 2.26-2.20 (m, 2H), 1.45 (s, 9H).

Workup

  1. washwas washed with 50 mL of water, organic phase
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (silica gel. 200-300 mesh, eluting with ethyl acetate/petroleum ether=1/1)

Sources & evidence

ORD record
ord-ab6eb106488a4d38a6eca6d1fe9d75d2
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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