Methanesulfonyl chloride → HCID 59725828, compound

HRID 545299Notes

Reaction equation

HRID 545299 reaction equation
[N:1]1([C:10]2[CH:23]=[CH:22][C:13]([C:14]([N:16]3[CH2:20][CH2:19][C@@H:18]([OH:21])[CH2:17]3)=[O:15])=[CH:12][CH:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.C(N(C(C)C)CC)(C)C.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>ClCCl>[CH3:33][S:34]([O:21][C@@H:18]1[CH2:19][CH2:20][N:16]([C:14](=[O:15])[C:13]2[CH:22]=[CH:23][C:10]([N:1]3[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=[CH:2]3)=[CH:11][CH:12]=2)[CH2:17]1)(=[O:36])=[O:35]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 59725830HCID 59725830, compound

Product 1

HCID 59725828HCID 59725828, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of (3R)-1-[4-(1H-benzimidazol-1-yl)benzoyl]pyrrolidin-3-ol (2.30 g, 7.48 mmol) in anhydrous dichloromethane at 0° C. is treated with diisopropylethyl amine (2.13 g, 16.46 mmol) and methanesulfonyl chloride (1.29 g, 11.22 mmol), stirred at 0° C. for 2 hours and concentrated to give a crude oil. Purification of this oil by flash column chromatography (silica, methanol:dichloromethane 5:95) provides the title product as a yellow solid, 2.3 g (81% yield), identified by NMR and mass spectral analyses. MS [386.5 m/e (M+H)].

Workup

  1. concentrationconcentrated
  2. customto give a crude oil
  3. customPurification of this oil by flash column chromatography (silica, methanol:dichloromethane 5:95)

Sources & evidence

ORD record
ord-8aff09dba25d4a9cb22d642858e511ee
Source dataset
uspto-grants-2011_05
Patent number
US07935719B2

Reaction notes

Loading…