Sodium hydride → HCID 59837297, compound

HRID 2358514Notes

Reaction equation

HRID 2358514 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22](C)[CH2:23][CH:24](O)[CH:25]([NH:28][C:29]([O:31][C:32](C)(C)C)=[O:30])[CH2:26][OH:27])=[C:18]([Cl:38])[CH:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][C:25]3([CH2:26][OH:27])[CH2:32][O:31][C:29](=[O:30])[NH:28]3)=[C:18]([Cl:38])[CH:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 68458841HCID 68458841, compound

Product 1

HCID 59837297HCID 59837297, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]propyl-2-t-butoxycarbonylamino-1,3-propanediol (3.30 g) was dissolved in THF (80 mL). At 0° C., 60% sodium hydride (600 mg) was added and the mixture was stirred at room temperature for 24 hours. To the resulting reaction mixture, ice water was added and the mixture was extracted with ethyl acetate. The extract was washed sequentially with water and a saturated aqueous solution of sodium hydroxide, and the organic phase was dried over anhydrous sodium sulfate. The solvent was removed and the residue was purified on a silica gel column chromatography (hexane:ethyl acetate=1:1 and then ethyl acetate alone) to give the desired product as a pale yellow oil (2.37 g).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed sequentially with water
  4. dry with materiala saturated aqueous solution of sodium hydroxide, and the organic phase was dried over anhydrous sodium sulfate
  5. customThe solvent was removed
  6. customthe residue was purified on a silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-5616dd98964142b2b2bc1b70262b90c7
Source dataset
uspto-grants-2010_07
Patent number
US07763752B2

Reaction notes

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