Acetic Acid → HCID 58932988, compound

HRID 2356786Notes

Reaction equation

FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][NH:22][C:23]([C:25]2[C:33]3[N:32]=[C:31]([CH:34]([CH3:36])[CH3:35])[NH:30][C:29]=3[CH:28]=[CH:27][CH:26]=2)=[O:24])[CH2:17][CH2:16]1)=O)(C)(C)C.C(N(CC)CC)C.C(O)(=O)C>ClCCl>[NH:15]1[CH2:20][CH2:19][CH:18]([CH2:21][NH:22][C:23]([C:25]2[C:33]3[N:32]=[C:31]([CH:34]([CH3:36])[CH3:35])[NH:30][C:29]=3[CH:28]=[CH:27][CH:26]=2)=[O:24])[CH2:17][CH2:16]1

Participants

Conditions

Temperature: 25 °C

Procedure

Trifluoroacetic acid (56.0 mL, 10 eq) was added to a flask containing a ˜5° C. solution of 4-{[(2-isopropyl-1H-benzoimidazole-4-carbonyl)amino]methyl}-piperidine-1-carboxylic acid tert-butyl ester (30.0 g, 1.0 eq) in dichloromethane (300 mL) while maintaining the temperature below 10° C. The resulting mixture was stirred at 20-30° C. for 2 h. When the reaction was complete, triethylamine (73.2 mL, 7.0 eq) and acetic acid (4.3 mL, 1.0 eq) were added to provide a solution of the title intermediate with an apparent pH of approximately 4 that was used directly in the next step.

Workup

temperaturewhile maintaining the temperature below 10° C

Sources & evidence

ORD record: ord-f95f97cb9ce243c69ca126b5fa193610
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759363B2

Reaction notes

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