Hydrochloric Acid → [2-(1-Cyano-3-methyl-butylcarbamoyl)-cyclohexyl]-carbamic acid benzyl ester

HRID 1593992Notes

Reaction equation

HRID 1593992 reaction equation
[CH2:1]([O:8][C:9](=[O:28])[NH:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[C:17](=[O:27])[NH:18][CH:19]([C:24](=O)[NH2:25])[CH2:20][CH:21]([CH3:23])[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.Cl>N1C=CC=CC=1>[CH2:1]([O:8][C:9](=[O:28])[NH:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[C:17](=[O:27])[NH:18][CH:19]([C:24]#[N:25])[CH2:20][CH:21]([CH3:23])[CH3:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9845Trifluoroacetic anhydrideHCID 20732578[2-(1-Carbamoyl-3-methyl-butylcarbamoyl)-cyclohexyl]-carbamic acid benzyl ester

Product 1

HCID 20732579[2-(1-Cyano-3-methyl-butylcarbamoyl)-cyclohexyl]-carbamic acid benzyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a 0° C. solution of the amide of step 3 (13.2 g, 33.9 mmol) in 150 mL of anhydrous pyridine was added trifluoroacetic anhydride (5.50 mL, 38.9 mmol) dropwise slowly over a 3 min period. The reaction mixture was stirred for 15 min and then poured into a slurry of ice and 1N HCl solution. The mixture was extracted with 500 mL of ethyl acetate, and washed with three 400 mL portions of 1N HCl, 400 mL of water, dried over sodium sulfate, filtered and concentrated to give a crude solid. Recrystallization from ethyl acetate/hexanes gave 11.3 g of [2-(1-Cyano-3-methyl-butylcarbamoyl)-cyclohexyl]-carbamic acid benzyl ester as a white solid. Yield: 90%, MS: 394 (M+Na+), mp=103.6-106.5° C.

Workup

  1. extractionThe mixture was extracted with 500 mL of ethyl acetate
  2. washwashed with three 400 mL portions of 1N HCl, 400 mL of water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude solid
  7. customRecrystallization from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-bc423b0b15aa42a5945bed9994fd58e4
Source dataset
uspto-grants-2007_11
Patent number
US07300934B2

Reaction notes

Loading…