Triethylamine → (1S)-2-[(tert-butoxycarbonyl)amino]-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl methanesulfonate

HRID 132804Notes

Reaction equation

HRID 132804 reaction equation
[CH3:1][C:2]1([CH3:18])[O:6][C@@H:5]([C@@H:7]([OH:17])[CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:4][O:3]1.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>ClCCl>[CH3:26][S:27]([O:17][C@H:7]([C@H:5]1[CH2:4][O:3][C:2]([CH3:18])([CH3:1])[O:6]1)[CH2:8][NH:9][C:10]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:16])(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 14249481Tert-Butyl (2S)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyethylcarbamate

Product 1

HCID 86591233(1S)-2-[(tert-butoxycarbonyl)amino]-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Alcohol 24 was dissolved in dichloromethane and cooled to 0°. Triethylamine and methanesulfonyl chloride were added and the solution stirred until the reaction was completed. The solution was extracted and the solvent removed to obtain the mesylate (25) which was purified using silica gel column chromatography. Solvent removal afforded a liquid.

Workup

  1. temperaturecooled to 0°
  2. extractionThe solution was extracted
  3. customthe solvent removed

Sources & evidence

ORD record
ord-e3ce7e39b401434080fb9e3ab3859716
Source dataset
uspto-grants-2008_06
Patent number
US07388118B2

Reaction notes

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