Methanesulfonyl chloride → HCID 86635256, compound

HRID 1363011Notes

Reaction equation

HRID 1363011 reaction equation
[CH:1]1([S:6][CH2:7][CH2:8][CH2:9][OH:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[CH3:20][S:21]([O:10][CH2:9][CH2:8][CH2:7][S:6][CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)(=[O:23])=[O:22]

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 63115554HCID 63115554, compound2×

Product 1

HCID 86635256HCID 86635256, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 3-(cyclopentylthio)-1-propanol (for example, as prepared for Intermediate 23) (1.05 g, 6.56 mmol) in dry DCM (5 ml) was added diisopropylethylamine (1.37 ml, 7.87 mmol), and then methanesulfonyl chloride (commercially available, for example, from Aldrich) (0.609 ml, 7.87 mmol) at 20° C. The reaction mixture was stirred at room temperature, under nitrogen for 2.5 h and then diluted with DCM (10 ml) and saturated sodium bicarbonate solution (20 ml). The phases were separated using a hydrophobic frit. The organic phase was concentrated in vacuo to afford the title compound (1.74 g): LCMS RT=3.13 min, ES+ve m/z 239 (M+H)+.

Workup

  1. customat 20° C
  2. customThe phases were separated
  3. concentrationThe organic phase was concentrated in vacuo

Sources & evidence

ORD record
ord-6f0bd1bbde5f40958d98a6e9a30cffcd
Source dataset
uspto-grants-2011_02
Patent number
US07884114B2

Reaction notes

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