Imidazole → HCID 88230374, compound

HRID 1368758Notes

Reaction equation

HRID 1368758 reaction equation
C(OC(N[C@H:9]([C@H:12](O)[CH2:13][Cl:14])[CH2:10][Cl:11])=O)(C)(C)C.[NH:16]1C=CN=C1.[Si](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])(C)C.CC[O:31][C:32](C)=[O:33]>CN(C=O)C.CN(C1C=CN=CC=1)C>[C:24]([O:31][C:32]([NH:16][CH:10]([Cl:11])[CH2:9][CH2:12][CH2:13][Cl:14])=[O:33])([CH3:27])([CH3:26])[CH3:25]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 113689092R-(t-Boc)amino-1,4-dichloro-3S-hydroxybutane

Product 1

HCID 88230374HCID 88230374, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 2(R)-(t-butyloxycarbonyl)amino-1,4-dichloro-3(S)-hydroxybutane (100.0 mg, 0.389 mmol) in dry DMF (2.5 mL) were added imidazole (79.4 mg, 1.67 mmol), DMAP (4.8 mg, 0.039 mmol) and TBS-Cl (175.9 mg, 1.167 mmol) at room temperature under N2. The resulting solution was stirred at 50° C. for 12 h. The reaction mixture was diluted with EtOAc (30 mL), washed with 0.1 N citric acid solution (5 mL), sat aqueous NaHCO3 (5 mL), water (5 mL) and brine (5 mL), dried over anhydrous magnesium sulfate, filtered, concentrated and column-chromatographed (10% EtOAc in n-Hex) to provide 2(S)-t-butyldimetylsilyloxy-3(R))-(t-butyloxycarbonyl)amino-1,4-dichlorobutane as a colorless solid (144.6 mg)

Workup

  1. washwashed with 0.1 N citric acid solution (5 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customcolumn-chromatographed (10% EtOAc in n-Hex)

Sources & evidence

ORD record
ord-0980e191f96c40d78480699f635c26ef
Source dataset
uspto-grants-2003_06
Patent number
US06573388B1

Reaction notes

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