HCID 53656947, compound → HCID 54079195, compound

HRID 1738296Notes

Reaction equation

HRID 1738296 reaction equation
FC1C(F)=C(F)C(F)=C(F)C=1[O:12][C:13](=O)[CH2:14][CH:15]([C:20](=[O:23])[NH:21][CH3:22])[CH2:16][CH:17]([CH3:19])[CH3:18].[CH2:25]([O:32][C:33](=[O:40])[CH2:34][NH:35][CH2:36][CH:37]([CH3:39])[CH3:38])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C>[CH2:25]([O:32][C:33](=[O:40])[CH2:34][N:35]([CH2:36][CH:37]([CH3:38])[CH3:39])[C:13](=[O:12])[CH2:14][CH:15]([C:20](=[O:23])[NH:21][CH3:22])[CH2:16][CH:17]([CH3:19])[CH3:18])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 53656947HCID 53656947, compoundHCID 54108658HCID 54108658, compound

Product 1

HCID 54079195HCID 54079195, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice-cooled solution of 5-methyl-3-methylcarbamoyl-hexanoic acid 2,3,4,5,6-pentafluorophenyl ester (350 mg, 0.99 mmol) in DMF (5 ml) was added isobutylamino-acetic acid benzyl ester (110 mg, 0.49 mmol) with stirring. The reaction mixture was allowed to warm to room temperature and stirred for 2 days then for 3 h at 50° C. The solvent was removed under reduced pressure, the residue was dissolved in ethyl acetate and the solution was washed successively with 1M HCl, 1M Na2CO3 and brine. The organic layer was dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography (silica gel, 50→100% ethyl acetate in hexane) to give the title compound as a colorless oil (130 mg, 70%). 1H-NMR; δ (CDCl3, rotamers), 7.33 (5H, m), 6.17 (1H, m), 5.15 (1H, m), 4.21 (1H, m), 3.91 (1H, m), 3.41-2.95 (2H, br m), 2.81 (2H, m), 2.75 (3H, m), 2.32 (1H, m), 1.91-1.40 (3H, br m), 1.28-1.05 (1H, m) and 0.85 (12H, m).

Workup

  1. stirringstirred for 2 days
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washthe solution was washed successively with 1M HCl, 1M Na2CO3 and brine
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography (silica gel, 50→100% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-9951c0b34c65416bb322c284e07831af
Source dataset
uspto-grants-1999_10
Patent number
US05962529

Reaction notes

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