Trifluoroacetic acid → HCID 68412122, compound

HRID 1662074Notes

Reaction equation

HRID 1662074 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][C@@H:15]([C:26]([NH:28][C@H:29]1[CH2:33][CH2:32][CH2:31][C@H:30]1[C:34]([O:36]CC1C=CC(OC)=CC=1)=[O:35])=[O:27])[NH:16][C:17]([C:19]1[N:23]([CH3:24])[N:22]=[C:21]([CH3:25])[CH:20]=1)=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][C@@H:15]([C:26]([NH:28][C@H:29]1[CH2:33][CH2:32][CH2:31][C@H:30]1[C:34]([OH:36])=[O:35])=[O:27])[NH:16][C:17]([C:19]1[N:23]([CH3:24])[N:22]=[C:21]([CH3:25])[CH:20]=1)=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68414056HCID 68414056, compound

Product 1

HCID 68412122HCID 68412122, compoundYield 9.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-methoxybenzyl (1R,2S)-2-({N5-[(benzyloxy)carbonyl]-N2-[(1,3-dimethyl-1H-pyrazole-5-yl)carbonyl]-L-ornithyl}amino)cyclopentanecarboxylate (0.50 g) and methylene chloride (5.0 ml) was added trifluoroacetic acid (5.0 ml) under ice-cooling, followed by stirring for 1 hour under ice-cooling. The reaction mixture was concentrated under reduced pressure, and diethyl ether and a saturated sodium bicarbonate solution were added to the residue. The organic layer was separated, the aqueous layer was then washed with diethyl ether, and citric acid was added thereto under ice-cooling. The solid precipitated was collected by filtration, washed with water, then purified by silica gel column chromatography (5% methanol/chloroform), solidified with a 50% aqueous ethanol solution, and washed to obtain (1R,2S)-2-({N5-[(benzyloxy)carbonyl]-N2-[(1,3-dimethyl-1H-pyrazole-5-yl)carbonyl]-L-ornithyl}amino)cyclopentanecarboxylic acid (37 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. concentrationThe reaction mixture was concentrated under reduced pressure, and diethyl ether
  4. additiona saturated sodium bicarbonate solution were added to the residue
  5. customThe organic layer was separated
  6. washthe aqueous layer was then washed with diethyl ether, and citric acid
  7. additionwas added
  8. temperatureunder ice-cooling
  9. customThe solid precipitated
  10. filtrationwas collected by filtration
  11. washwashed with water
  12. custompurified by silica gel column chromatography (5% methanol/chloroform)
  13. washwashed

Sources & evidence

ORD record
ord-73b20fbfd4ec473f9e411be4f9ddad48
Source dataset
uspto-grants-2011_10
Patent number
US08030489B2

Reaction notes

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