Neopentyl glycol → HCID 59570984, compound

HRID 2192909Notes

Reaction equation

HRID 2192909 reaction equation
[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:38])[C@@H:15]([C:23]1[CH:28]=[CH:27][C:26]([S:29]([CH:32]2[CH2:34][CH2:33]2)(=[O:31])=[O:30])=[C:25]([CH:35]2[CH2:37][CH2:36]2)[CH:24]=1)[CH2:16][C@H:17]1[CH2:21][CH2:20][C:19](=[O:22])[CH2:18]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:39][C:40]([CH3:45])([CH2:43]O)[CH2:41][OH:42].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:38])[C@@H:15]([C:23]1[CH:28]=[CH:27][C:26]([S:29]([CH:32]2[CH2:34][CH2:33]2)(=[O:31])=[O:30])=[C:25]([CH:35]2[CH2:37][CH2:36]2)[CH:24]=1)[CH2:16][C@H:17]1[CH2:21][CH2:20][C:19]2([O:42][CH2:41][C:40]([CH3:45])([CH3:43])[CH2:39][O:22]2)[CH2:18]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 31344Neopentyl glycolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 59570999HCID 59570999, compound

Product 1

HCID 59570984HCID 59570984, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of (4R)-4-benzyl-3-{(2R)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-[(1R)-3-oxocyclopentyl]propanoyl}-1,3-oxazolidin-2-one (25.7 g), 2,2-dimethylpropane-1,3-diol (50 g), pyridinium paratoluenesulfonate (1.32 g), and toluene (205 mL) was stirred under heating and reflux for 6 hours. After leaving it to be cooled at room temperature, saturated aqueous sodium bicarbonate (100 mL) was added thereto and the aqueous layer was extracted with ethyl acetate (100 mL×2). The organic layer was combined, sequentially washed with 1 M aqueous sodium hydroxide solution (50 mL), saturated aqueous ammonium chloride solution (50 mL), and saturated brine (50 mL), and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain (4R)-4-benzyl-3-{(2R)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-[(2R)-8,8-dimethyl-6,10-dioxaspiro[4.5]dec-2-yl]propanoyl}-1,3-oxazolidin-2-one (29.8 g) as a colorless amorphous substance.

Workup

  1. temperatureunder heating
  2. temperaturereflux for 6 hours
  3. customAfter leaving it
  4. extractionthe aqueous layer was extracted with ethyl acetate (100 mL×2)
  5. washsequentially washed with 1 M aqueous sodium hydroxide solution (50 mL), saturated aqueous ammonium chloride solution (50 mL), and saturated brine (50 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ffd3e8a1599d4ad69f004752ac480e8c
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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