2,6-Bis(trifluoromethyl)benzoic acid → N-Benzoyl-L-valyl-L-alanyl-L-norleucine 2,6-bis (trifluoromethyl)benzoyloxy methyl ketone

HRID 1636326Notes

Reaction equation

HRID 1636326 reaction equation
[F-].[K+].[F:3][C:4]([F:19])([F:18])[C:5]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[C:6]=1[C:7]([OH:9])=[O:8].Br[CH2:21][C:22](CBr)=[O:23].[C:26]([NH:34][C@H:35]([C:39]([NH:41][C@H:42]([C:44]([NH:46][C@H:47]([C:52]([OH:54])=[O:53])[CH2:48][CH2:49][CH2:50][CH3:51])=[O:45])[CH3:43])=[O:40])[CH:36]([CH3:38])[CH3:37])(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C=O)C>[CH3:21][C:22]([O:8][C:7](=[O:9])[C:6]1[C:5]([C:4]([F:18])([F:19])[F:3])=[CH:13][CH:12]=[CH:11][C:10]=1[C:14]([F:15])([F:17])[F:16])=[O:23].[C:26]([NH:34][C@H:35]([C:39]([NH:41][C@H:42]([C:44]([NH:46][C@H:47]([C:52]([OH:54])=[O:53])[CH2:48][CH2:49][CH2:50][CH3:51])=[O:45])[CH3:43])=[O:40])[CH:36]([CH3:37])[CH3:38])(=[O:33])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 906182,6-Bis(trifluoromethyl)benzoic acidHCID 522689Potassium FluorideHCID 88025812N-Benzoyl-L-valyl-L-alanyl-L-norleucine bromomethyl ketone

Product 1

HCID 86755192N-Benzoyl-L-valyl-L-alanyl-L-norleucine 2,6-bis (trifluoromethyl)benzoyloxy methyl ketone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of potassium fluoride (0.1 mmol, 6 mg) and 2,6-bis(trifluoromethyl)benzoic acid (0.066 mmol, 17 mg) in dry DMF (500 μl) was stirred over molecular sieves at room temperature for 5 minutes. A solution of N-benzoyl-L-valyl-L-alanyl-L-norleucine bromomethyl ketone (0.033 mmol), 16 mg) in dry DMF (500 μl) was added and the reaction mixture stirred for 1 hour. The reaction mixture was passed through a short silica plug and washed with 5% methanol in dichloromethane. Solvent was removed under vacuum and the residue purified using prep. HPLC. Freeze drying afforded (6.4 mg) as a white lyophilisate. Electrospray MS m/z 660 [MH+ ]. ##STR6##

Workup

  1. stirringthe reaction mixture stirred for 1 hour
  2. washwashed with 5% methanol in dichloromethane
  3. customSolvent was removed under vacuum
  4. customthe residue purified
  5. customFreeze drying
  6. customafforded (6.4 mg) as a white lyophilisate

Sources & evidence

ORD record
ord-dc53e240f2b845d6bcf1b7375fe81ed9
Source dataset
uspto-grants-2000_03
Patent number
US06034066

Reaction notes

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