Triethylamine → HCID 131725059, compound

HRID 584157Notes

Reaction equation

HRID 584157 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:30]=[CH:29][C:8]([O:9][CH2:10][C:11](=[O:28])[CH:12]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:17][CH:16]=2)[CH3:13])=[CH:7][CH:6]=1.C(N(CC)CC)C.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>ClCCl>[CH3:38][S:39]([O:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH2:10][C:11](=[O:28])[CH:12]([O:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])=[CH:19][CH:20]=2)[CH3:13])=[CH:29][CH:30]=1)(=[O:41])=[O:40]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86759793HCID 86759793, compound

Product 1

HCID 131725059HCID 131725059, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (3R and 3S)-1-[4-(3-hydroxypropyl)phenoxy]-3-[4-(tert-butoxycarbonyl)phenoxy]-2-butanone (1.57 g, 3.8 mmol) in dry dichloromethane (25 ml) was cooled to 0-50° C. and treated with triethylamine (1.1 ml, 7.9 mmol) followed by methanesulfonyl chloride (0.5 mL, 6.46 mmol) added dropwise over 2 minutes. After 45 minutes at 0-5° C., the reaction mixture was quenched by addition of ethyl acetate and saturated sodium bicarbonate. The organic phase was washed with brine and dried (anhydrous magnesium sulfate) and evaporated. Chromatography of the residual oil on silica gel (elution toluene-ethyl acetate, 9:1) gave 1.83 g (97%) of the title material as an oil.

Workup

  1. additionadded dropwise over 2 minutes
  2. customthe reaction mixture was quenched by addition of ethyl acetate and saturated sodium bicarbonate
  3. washThe organic phase was washed with brine
  4. dry with materialdried (anhydrous magnesium sulfate)
  5. customevaporated

Sources & evidence

ORD record
ord-3fa81723c91649589764495e77b9d56b
Source dataset
uspto-grants-2005_08
Patent number
US06924391B2

Reaction notes

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