Methanesulfonyl chloride → HCID 23449785, compound

HRID 1755131Notes

Reaction equation

HRID 1755131 reaction equation
[CH3:1][C:2]([O:5][C:6](=[O:12])[N:7]([CH2:9][CH2:10][OH:11])[CH3:8])([CH3:4])[CH3:3].[S:13](Cl)([CH3:16])(=[O:15])=[O:14]>N1C=CC=CC=1.C(Cl)Cl>[C:2]([O:5][C:6]([N:7]([CH3:8])[CH2:9][CH2:10][O:11][S:13]([CH3:16])(=[O:15])=[O:14])=[O:12])([CH3:1])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 545700N-(tert-Butoxycarbonyl)-N-methyl-2-aminoethanol

Product 1

HCID 23449785HCID 23449785, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

(2-Hydroxyethyl)methylcarbamic acid 1,1-dimethylethyl ester (350 mg, 2.0 mmol) was dissolved in pyridine (2 ml). Mesyl chloride (0.229 ml, 2.1 mmol) was added at room temperature, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was diluted with methylene chloride, and the organic layer was washed with a saturated aqueous sodium bicarbonate solution, dried over MgSO4 and concentrated under reduced pressure to give methanesulfonic acid 2-(tert-butoxycarbonyl-methyl-amino)-ethyl ester. This was used in the next reaction without complete purification.

Workup

  1. washthe organic layer was washed with a saturated aqueous sodium bicarbonate solution
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8ed846b3b4514e90b5ef499c1ddde3f4
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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