HCID 57189028, compound → HCID 18636015, compound

HRID 1085005Notes

Reaction equation

HRID 1085005 reaction equation
C[O:2][P:3]([CH2:23][N:24]1[C:28](=[O:29])[CH:27]=[C:26]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:25]1=[O:34])([CH2:5][CH:6]([C:11](=[O:22])[NH:12][C@H:13]([C:18](=[O:21])[NH:19][CH3:20])[CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:7][CH:8]([CH3:10])[CH3:9])=[O:4]>FC(F)(F)C(O)=O>[CH2:30]([C:26]1[C:25]([N:24]([CH2:23][P:3]([CH2:5][CH:6]([C:11](=[O:22])[NH:12][C@H:13]([C:18](=[O:21])[NH:19][CH3:20])[CH2:14][CH:15]([CH3:16])[CH3:17])[CH2:7][CH:8]([CH3:10])[CH3:9])(=[O:2])[OH:4])[C:28](=[O:29])[CH:27]=1)=[O:34])[CH:31]([CH3:32])[CH3:33]

Participants

3

Reactant 1

HCID 57189028HCID 57189028, compound

Product 1

HCID 18636015HCID 18636015, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

0.145 g (0.29 mmol) of [(2-isobutylmaleimido)methyl][(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl]phosphinic acid methyl ester was dissolved in 3 ml of trifluoroacetic acid and the solution was stirred at room temperature for 5 hours. After evaporation, the crude product was chromatographed on silica gel using chloroform/methanol/acetic acid/water (120:15:3:2) for the elution. There were obtained 70 mg of [(2-isobutylmaleimido)methyl][(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl]phosphinic acid in the form of a foam.

Workup

  1. customAfter evaporation
  2. customthe crude product was chromatographed on silica gel
  3. washfor the elution

Sources & evidence

ORD record
ord-96e2850fe1a44469bf931a1a260a7020
Source dataset
uspto-grants-1991_04
Patent number
US05006651

Reaction notes

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