Sodium Azide → HCID 86648400, compound

HRID 409462Notes

Reaction equation

HRID 409462 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([N:13]([CH2:16][C:17]2[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([C:27]([F:30])([F:29])[F:28])[CH:18]=2)[C:14]#[N:15])[CH2:10][C@H:9]1[CH2:31][CH3:32])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:33]=[N+:34]=[N-:35].[Na+]>CN(C=O)C.O>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([N:13]([CH2:16][C:17]2[CH:22]=[C:21]([C:23]([F:25])([F:24])[F:26])[CH:20]=[C:19]([C:27]([F:30])([F:28])[F:29])[CH:18]=2)[C:14]2[N:33]=[N:34][NH:35][N:15]=2)[CH2:10][C@H:9]1[CH2:31][CH3:32])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86648401HCID 86648401, compound

Product 1

HCID 86648400HCID 86648400, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of the crude (2R,4S)-4-[(3,5-bis-trifluoromethyl-benzyl)-cyano-amino]-2-ethyl-pyrrolidine-1-carboxylic acid tert-butylester (52 mg, 0.11 mmol), sodium azide (72 mg, 1.11 mmol) ammonium chloride (60 mg, 1.11 mmol) in DMF (2 mL) is stirred at 90° C. for 12 hours. The reaction mixture is diluted with water after letting it cool to room temperature. The product is extracted twice with EtOAc. The combined organic layer is washed with water and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The obtained residue is passed through silica pad (eluent: n-hexane/EtOAc) to give crude (2R,4S)-4-[(3,5-bis-trifluoromethyl-benzyl)-(2H-tetrazol-5-yl)-amino]-2-ethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (52 mg).

Workup

  1. extractionThe product is extracted twice with EtOAc
  2. washThe combined organic layer is washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-211343ad3323404db3f2dbf83a79b487
Source dataset
uspto-grants-2014_06
Patent number
US08759365B2

Reaction notes

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