Trifluoroacetic acid → HCID 11998032, compound

HRID 2246850Notes

Reaction equation

HRID 2246850 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH2:14][N:13]3[C:21]([C:24]([NH:26][CH2:27][CH:28]4[CH2:33][CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29]4)=[O:25])=[CH:22][CH2:23][C:12]3=[CH:11]2)=[O:9])[CH:5]=[CH:4][C:3]=1[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=1[CH3:47].FC(F)(F)C(O)=O>ClCCl>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH2:14][N:13]3[C:21]([C:24]([NH:26][CH2:27][CH:28]4[CH2:33][CH2:32][CH2:31][NH:30][CH2:29]4)=[O:25])=[CH:22][CH:23]=[C:12]3[CH2:11]2)=[O:9])[CH:5]=[CH:4][C:3]=1[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=1[CH3:47]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86609046HCID 86609046, compound

Product 1

HCID 11998032HCID 11998032, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 3-{[({10-[(2,2′-dimethyl-1,1′-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}carbonyl)amino]methyl}piperidine-1-carboxylate of Step A (0.42 g, 0.66 mmol) in dry dichloromethane (3 mL) was added trifluoroacetic acid (0.51 mL, 6.6 mmol) and the reaction mixture stirred at room temperature under nitrogen for 20 hours. The reaction mixture was then diluted with dichloromethane (50 mL), washed with 1 M sodium hydroxide solution (50 mL) and brine (50 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to afford a pink glass. Purification by flash chromatography using a solvent gradient of 2.5 to 10% ammonia saturated methanol in dichloromethane gave a pale yellow oil (0.31 g). Crystallization from diethyl ether (2 mL) afforded the title compound (0.19 g) as a pale yellow solid.

Workup

  1. washwashed with 1 M sodium hydroxide solution (50 mL) and brine (50 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto afford a pink glass
  6. customPurification by flash chromatography

Sources & evidence

ORD record
ord-c6f290da128243c5b41f3c2678a2439b
Source dataset
uspto-grants-2010_03
Patent number
US07687623B2

Reaction notes

Loading…