Trifluoroacetic acid → HCID 14373552, compound

HRID 630641Notes

Reaction equation

HRID 630641 reaction equation
Cl.N[C@@H:3]([CH2:22]CC1C=CC=CC=1)[C:4]([NH:6][C@@H](CC(C)C)C(OCC1C=CC=CC=1)=O)=[O:5].CC(C)C[C@H](NC(=O)[C@@H](NC(=O)CN1CCOCC1)CCC1C=CC=CC=1)C([NH:36][C@@H](CC1C=CC=CC=1)C(N[C@@H](CC(C)C)C([C@@]1(C)CO1)=O)=O)=O.[C:82]([OH:88])([C:84](F)(F)F)=[O:83]>CO>[NH:6]([C:4](=[O:5])[CH2:3][CH2:22][CH2:84][C:82]([OH:88])=[O:83])[NH2:36]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11556711CarfilzomibHCID 86715396HCID 86715396, compound

Product 1

HCID 14373552HCID 14373552, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Referring to FIG. 44, 5-hydrazinyl-5-oxopentanoic acid (2, 0.600 g, 4.14 mmol), (S)-4-methyl-N—((S)-1-(((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamide (1.97 g, 2.74 mmol) and TFA (100 μl) in methanol (20 ml) were stirred at room temperature for 5 days. The mixture was evaporated and the residue purified by prep HPLC (C18 column, acetonitrile/water) to give product as an oil; (601 mg, 29%).

Workup

  1. customThe mixture was evaporated
  2. customthe residue purified by prep HPLC (C18 column, acetonitrile/water)
  3. customto give product as an oil

Sources & evidence

ORD record
ord-f0b0c7cdb1114d2aab3bddc33fd4652f
Source dataset
uspto-grants-2016_04
Patent number
US09315542B2

Reaction notes

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