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Triethylamine → Methanesulfonic acid (S)-3-(2,6-dimethoxy-phenoxy)-2-methanesulfonyloxy-propyl ester

HRID 453832
Notes
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Reaction equation

HRID 453832 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[C:4]=1[O:5][CH2:6][C@H:7]([OH:10])[CH2:8][OH:9].[CH2:17](N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26].[OH:29][S:30]([O-:33])(=O)=O.[Na+]>ClCCl>[CH3:16][O:15][C:11]1[CH:12]=[CH:13][CH:14]=[C:3]([O:2][CH3:1])[C:4]=1[O:5][CH2:6][C@H:7]([O:10][S:30]([CH3:17])(=[O:33])=[O:29])[CH2:8][O:9][S:25]([CH3:24])(=[O:27])=[O:26]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516919Sodium BisulfateHCID 10799347(R)-3-(2,6-Dimethoxyphenoxy)propane-1,2-diol

Product 1

HCID 86644725Methanesulfonic acid (S)-3-(2,6-dimethoxy-phenoxy)-2-methanesulfonyloxy-propyl ester

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Procedure

(R)-3-(2,6-Dimethoxyphenoxy)propane-1,2-diol (2.26 g, 9.90 mmol) in dichloromethane (20 ml) was cooled to 0° C. and stirred under nitrogen atmosphere. Triethyl amine (2.94 g, 29.00 mmol) was added in 15 min. Methanesulfonic acid chloride (2.61 g, 21.80 mmol) was added, and the mixture was stirred at +25° C. for 3 h. Dichloromethane (20 ml) and 1 M NaHSO4 solution (10 ml) were added and the layers were separated. Organic layer was washed with 1 M NaHSO4 solution (10 ml), water (10 ml) and saturated sodium chloride solution (10 ml), dried (Na2SO4), filtered and evaporated to dryness to give 3.08 g of the title compound.

Workup

  1. stirringthe mixture was stirred at +25° C. for 3 h
  2. customthe layers were separated
  3. washOrganic layer was washed with 1 M NaHSO4 solution (10 ml), water (10 ml) and saturated sodium chloride solution (10 ml)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-d83d2cf3d8744bd3b05315bb617bcef5
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08492549B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes