Water → HCID 89851361, compound

HRID 627215Notes

Reaction equation

HRID 627215 reaction equation
O[C:2]([C@H:7]1[CH2:11][O:10][C:9]([CH3:13])([CH3:12])[N:8]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])([CH2:5][CH3:6])[CH2:3][CH3:4].C(N(CC)CC)C.CS(Cl)(=O)=O.O>ClCCl.C(OCC)C>[CH3:13][C:9]1([CH3:12])[N:8]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[C@@H:7]([C:2]([CH2:5][CH3:6])=[CH:3][CH3:4])[CH2:11][O:10]1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 89851480(R)-tert-butyl 4-(3-hydroxypentan-3-yl)-2,2-dimethyloxazolidine-3-carboxylate2×

Product 1

HCID 89851361HCID 89851361, compoundYield 71.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-tert-butyl 4-(3-hydroxypentan-3-yl)-2,2-dimethyloxazolidine-3-carboxylate (Intermediate 200, 26.4 g, 91.86 mmol) in dichloromethane (350 mL) at 0° C. was added triethylamine (128 mL, 918.60 mmol) and then slowly added methanesulfonyl chloride (35.8 mL, 459.30 mmol). The yellow reaction mixture was warmed to room temperature and stirred overnight for ˜16 h. The reaction mixture was diluted with diethyl ether and poured into water. The organic layer was washed with 10% citric acid, saturated sodium bicarbonate, saturated sodium chloride, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give a brown oil. Purification by flash column chromatography (0-20% ethyl acetate/hexanes) afforded the title compound (17.70 g, 71.5%) as very pale yellow oil.

Workup

  1. washThe organic layer was washed with 10% citric acid, saturated sodium bicarbonate, saturated sodium chloride
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto give a brown oil
  6. customPurification by flash column chromatography (0-20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-0f05638d3b814af98bd3f48fb986f717
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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