HCID 19083200, compound → HCID 54415848, compound

HRID 963687Notes

Reaction equation

HRID 963687 reaction equation
C([O:5][C:6](=[O:30])[CH:7]([CH:11]([C:16](=[O:29])[NH:17][CH:18]([C:23](=[O:28])[NH:24][CH:25]1[CH2:27][CH2:26]1)[C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:8][CH:9]=[CH2:10])(C)(C)C>ClCCl.C(O)(C(F)(F)F)=O>[CH:25]1([NH:24][C:23]([CH:18]([NH:17][C:16]([CH:11]([CH:7]([CH2:8][CH:9]=[CH2:10])[C:6]([OH:30])=[O:5])[CH2:12][CH:13]([CH3:15])[CH3:14])=[O:29])[C:19]([CH3:21])([CH3:22])[CH3:20])=[O:28])[CH2:27][CH2:26]1

Participants

4

Reactant 1

HCID 19083200HCID 19083200, compound

Product 1

HCID 54415848HCID 54415848, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

2-[1-(1-Cyclopropylcarbamoyl-2,2-dimethyl-propylcarbamoyl)-3-methyl-butyl]-pent-4-enoic acid-tert-butyl ester (2.05 g, 4.83 mmol) was dissolved in dichloromethane (7 ml) and TFA (7 ml). The mixture was allowed to stand at 0°-5° C. overnight then solvent was evaporated under reduced pressure, azeotroping with three times toluene to provide the title compound as a white solid which was recrystallised from ethyl acetate. Yield: 1.81 g (74%). 1H-NMR; δ (CD3OD), 8.19 (1H, br s), 7.95 (1H, d, J=9.2 Hz), 5.72 (1H, m), 4.98 (2H, m), 4.19 (1H, d, J=9.3 Hz), 2.76 (1H,m), 2.56 (2H, m) 2.23 (1H, m), 1.59 (1H, m), 1.37 (1H, m), 0.96 (9H, s), 0.87 (3H, d,J=6.5 Hz), 0.81 (3H, d, J=6.6 Hz), 0.68 (2H, m) and 0.43 (2H, m).

Workup

  1. customsolvent was evaporated under reduced pressure
  2. customazeotroping with three times toluene

Sources & evidence

ORD record
ord-df60df56555f4d7683cc9f51ab4ce2e4
Source dataset
uspto-grants-1998_06
Patent number
US05763621

Reaction notes

Loading…