Sodium Azide → HCID 86762376, compound

HRID 2369817Notes

Reaction equation

HRID 2369817 reaction equation
CC1C=CC(S(O[CH2:12][C@@H:13]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=O)=O)=CC=1.[N-:28]=[N+:29]=[N-:30].[Na+]>CN(C)C=O.O.C(OCC)(=O)C>[N:28]([CH2:12][C@@H:13]([NH:20][C:21](=[O:22])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[N+:29]=[N-:30]

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 10894464(2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethyl 4-methylbenzenesulfonate

Product 1

HCID 86762376HCID 86762376, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

The mixture of (2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethyl 4-methylbenzenesulfonate (350 mg, 0.9 mmol, 1.0 eq.) and sodium azide (117 mg, 1.8 mmol, 2.0 eq.) in N,N-dimethylformamide (5 ml) was stirred at 65° C. overnight. The mixture was cooled to room temperature and diluted with water and ethyl acetate. The organic layer was separated and washed with brine, dried, and concentrated to afford tert-butyl [(1S)-2-azido-1-phenylethyl]carbamate in 90% yield.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4e1d86bd2a464e67877e86729d28223b
Source dataset
uspto-grants-2014_04
Patent number
US08710044B2

Reaction notes

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