Water → tert-Butyl N-(2-((methylsulfonyl)oxy)ethyl)carbamate

HRID 30535Notes

Reaction equation

HRID 30535 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)C(C)C)(C)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23].O>ClCCl>[C:4]([O:3][C:1]([NH:8][CH2:9][CH2:10][O:11][S:22]([CH3:21])(=[O:24])=[O:23])=[O:2])([CH3:5])([CH3:6])[CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamate

Product 1

HCID 22605302tert-Butyl N-(2-((methylsulfonyl)oxy)ethyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Boc-glycinol (25.0 g, 155 mmol) and N,N-diisopropylethylamine (32.4 mL, 186 mmol) in anhydrous dichloromethane (70 mL) was added methanesulfonyl chloride (19.5 mL, 171 mmol) dropwise under ice-water cooling. The mixture was stirred at room temperature for 2 hours. Water was added to the mixture, and the product was extracted with CH2Cl2. The organic layer was dried over Na2SO4, and the solvent was removed in vacuo to give methanesulfonic acid 2-(tert-butoxycarbonylamino)ethyl ester as a crude oil (37 g, 99.7% yield) which was used for the next step without further purification.

Workup

  1. extractionthe product was extracted with CH2Cl2
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-3b06d10f87f54db6b1c4562944c027a9
Source dataset
uspto-grants-2008_09
Patent number
US07423175B2

Reaction notes

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