Hydrochloric Acid → HCID 25224005, compound

HRID 923460Notes

Reaction equation

HRID 923460 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:11]1[N:15](CCC#N)[N:14]=[N:13][N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N12CCCN=C1CCCCC2.Cl>ClCCl>[CH2:1]([O:8][CH2:9][C@H:10]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])[C:11]1[N:12]=[N:13][NH:14][N:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 131734986HCID 131734986, compound

Product 1

HCID 25224005HCID 25224005, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 400 mg of tert-butyl {(1R)-2-(benzyloxy)-1-[1-(2-cyanoethyl)-1H-tetrazol-5-yl]ethyl}carbamate in 10 ml of dichloromethane was added 0.9 ml of 1,8-diazabicyclo[5.4.0]undeca-7-ene, followed by stirring at room temperature for 2 hours. The reaction mixture was added to a mixture of ice and 1 M hydrochloric acid, followed by extraction with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and the solvent was then evaporated under reduced pressure to obtain 343 mg of tert-butyl [(1R)-2-(benzyloxy)-1-(2H-tetrazol-5-yl)ethyl]carbamate.

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was then evaporated under reduced pressure

Sources & evidence

ORD record
ord-d407f76e53fa45ca9ec4f69d69b4be55
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

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