Methanesulfonyl chloride → HCID 178505285, compound

HRID 2360291Notes

Reaction equation

HRID 2360291 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[NH:8][C:9]1[S:10][C:11]([CH2:18][CH2:19][OH:20])([CH2:15][CH2:16][OH:17])[C:12](=[O:14])[N:13]=1.C(N(C(C)C)CC)(C)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>C(Cl)Cl>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[NH:8][C:9]1[S:10][C:11]([CH2:15][CH2:16][O:17][S:31]([CH3:30])(=[O:33])=[O:32])([CH2:18][CH2:19][O:20][S:31]([CH3:30])(=[O:33])=[O:32])[C:12](=[O:14])[N:13]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 1785179402-(2-bicyclo[2.2.1]heptanylamino)-5,5-bis(2-hydroxyethyl)-1,3-thiazol-4-one

Product 1

HCID 178505285HCID 178505285, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-(bicyclo[2.2.1]heptan-2-ylamino)-5,5-bis(2-hydroxyethyl)thiazol-4(5H)-one (280 mg, 0.94 mmol) and diisopropylethylamine (Aldrich, 412 mg, 3.19 mmol) in CH2Cl2 (5 mL) was added methanesulfonyl chloride (344 mg, 3.00 mmol, 3.2 eq), and the reaction mixture was stirred at room temperature for 18 h. The reaction mixture was then concentrated in vacuo to provide the title compound which was used without further purification. MS (ESI, pos. ion) m/z: 455 (M+H).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-7e493889facd4cd585c28543a940d6e8
Source dataset
uspto-grants-2014_04
Patent number
US08686011B2

Reaction notes

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