Tetrahydrofuran → HCID 45091887, compound

HRID 34104

Reaction equation

HRID 34104 reaction equation
O1CCCC1.[BH4-].[Na+].[C:8]([O:12][C:13](=[O:31])[NH:14][CH:15]([C:26]1[O:27][CH:28]=[CH:29][N:30]=1)S(C1C=CC(C)=CC=1)(=O)=O)([CH3:11])([CH3:10])[CH3:9].[Cl-].[NH4+]>O>[C:8]([O:12][C:13](=[O:31])[NH:14][CH2:15][C:26]1[O:27][CH:28]=[CH:29][N:30]=1)([CH3:11])([CH3:9])[CH3:10]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 60034835[Oxazol-2-yl-(toluene-4-sulfonyl)-methyl]-carbamic Acid Tert-Butyl Ester

Product 1

HCID 45091887HCID 45091887, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 4 mL of tetrahydrofuran was added 51.4 mg of sodium borohydride, and added with 240 mg of [oxazole-2-yl-(toluene-4-sulfonyl)-methyl]-carbamic acid tert-butyl ester obtained by Production example 769 over 13 minutes at room temperature under stirring. Thereafter, the solution was stirred for another 2 hours and 30 minutes under room temperature, added with saturated aqueous ammonium chloride under ice cooling, and stirred for another 30 minutes under ice cooling. Thereafter, water was added, extracted twice with diethyl ether and dried over anhydrous magnesium sulfate. The solvent was evaporated, followed by purification and separation by silica gel column chromatography, to afford 72.3 mg of the title compound as colorless crystals.

Workup

  1. customobtained by Production example 769 over 13 minutes at room temperature
  2. stirringThereafter, the solution was stirred for another 2 hours and 30 minutes under room temperature
  3. stirringstirred for another 30 minutes under ice cooling
  4. extractionextracted twice with diethyl ether
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customfollowed by purification and separation by silica gel column chromatography

Sources & evidence

ORD record
ord-c140664bf10945baae4d8b114ad87691
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Linked notes

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