Trifluoroacetic acid → HCID 13942993, compound

HRID 260650Notes

Reaction equation

HRID 260650 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH:12]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:13]([NH:15][C@H:16]([C:22]([O:24][CH3:25])=[O:23])[CH2:17][CH2:18][CH2:19][CH:20]=O)=[O:14].FC(F)(F)C(O)=O.[OH-].[Na+]>C(Cl)Cl.O>[O:11]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2](=[O:1])[N:3]1[CH:12]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:13]([N:15]1[CH:20]=[CH:19][CH2:18][CH2:17][CH:16]1[C:22]([O:24][CH3:25])=[O:23])=[O:14]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 131719439HCID 131719439, compound

Product 1

HCID 13942993HCID 13942993, compoundYield 137%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Transfer the solution of [2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-6-oxo-(S)-norleucine, methyl ester in methylene chloride (volume about 4.5 L) to a 12-liter flask and place under nitrogen atmosphere. Stir and add trifluoroacetic acid (440 mL, 5.71 mole) in one portion. Stir the resulting mixture at room temperature for one hour, then rapidly cool to about 0° C. Add a solution of sodium hydroxide (240 g, 6.0 mole) in water (3.4 L) in a slow stream to the vigorously stirred mixture at such a rate that the pot temperature stays at about 0° C. Separate the organic phase and extract the aqueous phase with methylene chloride (1 L). Combine the organic phases and dry (MgSO4). Filter and remove the solvent in vacuo to leave a residue (262 g, 137%).

Workup

  1. stirringStir the resulting mixture at room temperature for one hour
  2. customstays at about 0° C
  3. customSeparate the organic phase
  4. extractionextract the aqueous phase with methylene chloride (1 L)
  5. dry with materialCombine the organic phases and dry (MgSO4)
  6. filtrationFilter
  7. customremove the solvent in vacuo

Sources & evidence

ORD record
ord-702c357f40304e4eaad7ed0cc8dfb64b
Source dataset
uspto-grants-1996_06
Patent number
US05529997

Reaction notes

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