Methanesulfonyl chloride → HCID 86717515, compound

HRID 712057Notes

Reaction equation

HRID 712057 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:5][C@@H:4]1[O:17][CH3:18].[CH3:19][S:20](Cl)(=[O:22])=[O:21]>ClCCl>[CH3:19][S:20]([O:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:16])[CH2:5][C@@H:4]1[O:17][CH3:18])(=[O:22])=[O:21]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 86717516HCID 86717516, compound

Product 1

HCID 86717515HCID 86717515, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl [(1S,3S,4R)-4-(hydroxymethyl)-3-methoxycyclohexyl]carbamate (racemic) (720 mg, 2.8 mmol) in dichloromethane (9 mL) was added methanesulfonyl chloride (0.430 mL, 5.56 mmol) at 0° C. The mixture was stirred at 0° C. for 1 h. The mixture was then concentrated and partitioned between ethyl acetate and water. The organic phase was concentrated and purified by flash chromatography (eluting with a gradient of 50% ethyl acetate in hexanes) to give the desired product (0.859 g, 92%). LCMS calculated for C9H20NO4S (M+H-Boc)+: m/z=238.1. Found: 238.0.

Workup

  1. concentrationThe mixture was then concentrated
  2. custompartitioned between ethyl acetate and water
  3. concentrationThe organic phase was concentrated
  4. custompurified by flash chromatography (
  5. washeluting with a gradient of 50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-fad0a06d13ce469abf562f2526f0100c
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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