Methanesulfonyl chloride → HCID 86717566, compound

HRID 712115Notes

Reaction equation

HRID 712115 reaction equation
[OH:1][CH2:2][CH:3]1[O:8][CH2:7][C@@H:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:5][CH2:4]1.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>ClCCl>[CH3:17][S:18]([O:1][CH2:2][CH:3]1[CH2:4][CH2:5][C@H:6]([NH:9][C:10]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:16])[CH2:7][O:8]1)(=[O:20])=[O:19]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 86717565(2ξ)-2,6-Anhydro-3,4,5-trideoxy-5-[[(1,1-dimethylethoxy)carbonyl]amino]-D-glycero-hexitol

Product 1

HCID 86717566HCID 86717566, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl [(3S)-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]carbamate (331 mg, 1.43 mmol) in dichloromethane (5 mL) was treated with methanesulfonyl chloride (0.222 mL, 2.87 mmol) at 0° C. The mixture was stirred at 0° C. for 1 h, then concentrated and partitioned between ethyl acetate and water. The organic phase was concentrated and purified on silica gel (eluting with a gradient of 0 to 50% ethyl acetate in hexanes) to give the desired product (0.38 g, 86%). LCMS calculated for C8H16NO6S (M-t-Bu+H)+: m/z=254.1. Found: 254.0.

Workup

  1. concentrationconcentrated
  2. custompartitioned between ethyl acetate and water
  3. concentrationThe organic phase was concentrated
  4. custompurified on silica gel (
  5. washeluting with a gradient of 0 to 50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-36cf46e072884ff188e2e22ec2409551
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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