Sodium 1-phenyl-1H-tetrazole-5-thiolate → HCID 67608356, compound

HRID 39402Notes

Reaction equation

HRID 39402 reaction equation
Cl[CH2:2][C@H:3]1[O:8][C:7]([CH3:10])([CH3:9])[O:6][C@@H:5]([CH2:11][C:12]([O:14][C:15]([CH3:24])([CH3:23])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:13])[CH2:4]1.[C:25]1([N:31]2[C:35]([S-:36])=[N:34][N:33]=[N:32]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[Na+]>CN(C)C=O>[CH3:9][C:7]1([CH3:10])[O:6][C@@H:5]([CH2:11][C:12]([O:14][C:15]([CH3:24])([CH3:23])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:13])[CH2:4][C@@H:3]([CH2:2][S:36][C:35]2[N:31]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:32]=[N:33][N:34]=2)[O:8]1

Participants

4

Reactant 2

HCID 2735174Sodium 1-phenyl-1H-tetrazole-5-thiolateHCID 676077022-methyl-1-phenylpropan-2-yl 2-((4R,6S)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

Product 1

HCID 67608356HCID 67608356, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

2-methyl-1-phenylpropan-2-yl 2-((4R,6S)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate (30 g) prepared in Example 5 was dissolved in dimethylformamide (150 ml), and sodium 1-phenyl-1H-tetrazole-5-thiolate (33.9 g) prepared in Example 7 was added thereto. The reaction liquid was warmed to 90° C. and then stirred for 24 hours. The reaction liquid was cooled to room temperature, and diisopropyl ether (600 ml) and purified water (600 ml) were added thereto. The organic layer was separated, washed with purified water (600 ml), a 10% sodium bicarbonate aqueous solution (600 ml), a saturated ammonium chloride aqueous solution (600 ml) and a saturated sodium chloride aqueous solution (600 ml), dried over anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure to give the title compound (40.8 g).

Workup

  1. customThe reaction liquid
  2. customThe reaction liquid
  3. temperaturewas cooled to room temperature
  4. customdiisopropyl ether (600 ml) and purified water (600 ml)
  5. additionwere added
  6. customThe organic layer was separated
  7. washwashed with purified water (600 ml)
  8. dry with materiala 10% sodium bicarbonate aqueous solution (600 ml), a saturated ammonium chloride aqueous solution (600 ml) and a saturated sodium chloride aqueous solution (600 ml), dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e35203b5d9c441788b6d42d1314f2686
Source dataset
uspto-grants-2013_09
Patent number
US08524914B2

Reaction notes

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