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

HRID 2366040Notes

Reaction equation

HRID 2366040 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]

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 6344DichloromethaneSolvent2×

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-4f7d5bd031d94ac680269aead1e261b8
Source dataset
uspto-grants-2014_04
Patent number
US08697723B2

Reaction notes

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