Sodium hydride → HCID 11371084, compound

HRID 1368759Notes

Reaction equation

HRID 1368759 reaction equation
[Si:1]([O:8][C@@H:9]([C@@H:12]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13]Cl)[CH2:10][Cl:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+].[Cl-].[NH4+]>C1COCC1>[C:19]([O:18][C:16]([N:15]1[CH2:13][C@@H:12]1[C@H:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:10][Cl:11])=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 111995852S-t-Butyldimethylsilyloxy-3R-(t-Boc)-amino-1,4-dichlorobutane

Product 1

HCID 11371084HCID 11371084, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a magnetically stirred solution of 2(S)-t-butyldimetylsilyloxy-3(R)-(t-butyloxycarbonyl)amino-1,4-dichlorobutane (375.4 mg, 1.008 mmol) in THF (10 mL) was added NaH slowly at 0° C. under N2. After 5 h, the reaction mixture was slowly added to sat aq ammonium chloride solution (40 mL) and ice (20 g). The resulting solution was extracted with EtOAc (60 mL 4). The combined organic layers were washed with brine (50 mL), dried over anhydrous magnesium sulfate, filtered, concentrated and column chromatographed (10% EtOAc in n-Hex) to provide N-t-butyloxycarbonyl-2(R)-(1(S)-t-butyldimetylsilyloxy-2-chloroethyl)aziridine (339.5 mg) as a colorless oil.

Workup

  1. additionthe reaction mixture was slowly added
  2. extractionThe resulting solution was extracted with EtOAc (60 mL 4)
  3. washThe combined organic layers were washed with brine (50 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customcolumn chromatographed (10% EtOAc in n-Hex)

Sources & evidence

ORD record
ord-4bede00db9f54e26b555ac1f881ace4b
Source dataset
uspto-grants-2003_06
Patent number
US06573388B1

Reaction notes

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