Triethylamine → (2R)-2-methanesulfonyloxy-2-((4S)-2-(3-acetoxy-2-methylphenyl)-4,5-dihydrooxazol-4-yl)ethanol

HRID 2271243Notes

Reaction equation

HRID 2271243 reaction equation
[CH3:1][S:2]([O:5][C@@H:6]1[C@@H:12]([NH:13][C:14](=[O:26])[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22](=[O:24])[CH3:23])[C:16]=2[CH3:25])[CH2:11]OC(C)(C)[O:8][CH2:7]1)(=[O:4])=[O:3].C(N(CC)CC)C>ClCCl>[CH3:1][S:2]([O:5][C@H:6]([C@@H:12]1[CH2:11][O:26][C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22](=[O:24])[CH3:23])[C:16]=2[CH3:25])=[N:13]1)[CH2:7][OH:8])(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 10787996(5R,6S)-N-(5-methanesulfonyloxy-2,2-dimethyl-1,3-dioxepan-6-yl)-3-acetoxy-2-methylbenzamide2×

Product 1

HCID 10689674(2R)-2-methanesulfonyloxy-2-((4S)-2-(3-acetoxy-2-methylphenyl)-4,5-dihydrooxazol-4-yl)ethanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(5R,6S)-N-(5-Methanesulfonyloxy-2,2-dimethyl1,3-dioxepan-6-yl)-3-acetoxy-2-methylbenzamide (compound [9], 34.2 g, 82.3 mmol) was dissolved in dichloromethane (340 ml) and boron trifluoride-diethyl ether complex (30.4 ml, 247 mmol) was added over 5 minutes with stirring at room temperature. The mixture was stirred for 40 hours at room temperature. Triethylamine (34.5 ml, 247 mmol) was added at not more than 15° C. and the solvent was distilled away under reduced pressure to 1/5 volume. The residue was diluted with ethyl acetate (340 ml) and washed successively with 10% brine (340 ml), 10% brine (340 ml) containing citric acid (17 g), and saturated brine (340 ml). After drying over magnesium sulfate, the solution was concentrated to 36 g to give a crude product of (2R)-2-methanesulfonyloxy-2-((4S)-2-(3-acetoxy-2-methylphenyl)-4,5-dihydrooxazol-4-yl)ethanol (compound [10]).

Workup

  1. additionboron trifluoride-diethyl ether complex (30.4 ml, 247 mmol) was added over 5 minutes
  2. stirringThe mixture was stirred for 40 hours at room temperature
  3. distillationthe solvent was distilled away under reduced pressure to 1/5 volume
  4. additionThe residue was diluted with ethyl acetate (340 ml)
  5. washwashed successively with 10% brine (340 ml), 10% brine (340 ml)
  6. additioncontaining citric acid (17 g), and saturated brine (340 ml)
  7. dry with materialAfter drying over magnesium sulfate
  8. concentrationthe solution was concentrated to 36 g

Sources & evidence

ORD record
ord-f56b608f35564723b1e919026044776f
Source dataset
uspto-grants-2001_12
Patent number
US06333416B2

Reaction notes

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