Ammonium Chloride → HCID 57572302, compound

HRID 1293232Notes

Reaction equation

HRID 1293232 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:10])=[CH:5][CH:4]=1)#[N:2].[N-:19]=[N+:20]=[N-:21].[Na+].[Cl-].[NH4+]>CN(C)C=O.CCOCC>[N:2]1[NH:19][N:20]=[N:21][C:1]=1[C:3]1[CH:4]=[CH:5][C:6]([C@@H:9]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:10])=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 59462304HCID 59462304, compound

Product 1

HCID 57572302HCID 57572302, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of tert-butyl [(1S)-1-(4-cyanophenyl)ethyl]carbamate (step 1, 1.11 g, 4.51 mmol), sodium azide (1.75 g, 27.1 mmol) and ammonium chloride (1.15 g, 27.1 mmol) in N,N-dimethylforamide (25 mL) was heated at 110° C. for 24 h. After cooling to room temperature, the mixture was diluted with ether (200 mL) and washed with 1 N hydrochloric acid (100 mL). The organic layer was dried over magnesium sulfate and evaporated. The residue was crystallized from dichloromethane and hexane to give 1.19 g (91%) of the title compounds as white solids: 1H-NMR (DMSO-d6) δ 7.98 (2H, d, J=8.3 Hz), 7.51 (2H, d, J=8.3 Hz), 4.74–4.63 (1H, m), 1.37–1.32 (12H, m); MS (ESI) m/z 290 (M+H)+, 288 (M−H)−.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with 1 N hydrochloric acid (100 mL)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customevaporated
  5. customThe residue was crystallized from dichloromethane and hexane

Sources & evidence

ORD record
ord-6af341a62b8c4abf9feb6311099dbe9b
Source dataset
uspto-grants-2007_07
Patent number
US07238714B2

Reaction notes

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