HCID 69734264, compound → HCID 86589157, compound

HRID 1062900Notes

Reaction equation

HRID 1062900 reaction equation
[CH2:1]([N:4]([CH2:25][CH2:26][CH3:27])[C:5]([C:7]1[CH:8]=[C:9]([CH:22]=[CH:23][CH:24]=1)[C:10]([NH:12][C@@H:13]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:14](OC)=[O:15])=[O:11])=[O:6])[CH2:2][CH3:3]>C1(C)C=CC=CC=1>[CH2:25]([N:4]([CH2:1][CH2:2][CH3:3])[C:5]([C:7]1[CH:8]=[C:9]([CH:22]=[CH:23][CH:24]=1)[C:10]([NH:12][C@@H:13]([CH2:18][CH:19]([CH3:21])[CH3:20])[CH:14]=[O:15])=[O:11])=[O:6])[CH2:26][CH3:27]

Participants

3

Reactant 1

HCID 69734264HCID 69734264, compound

Product 1

HCID 86589157HCID 86589157, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Methyl(2S)-2-({3-[(dipropylamino)carbonyl]benzoyl}amino)-4-methylpentanoate (1.65 g, 4.4 mmol) in 20 mL of toluene under nitrogen is cooled to −78° C. To this is added, dropwise over 5 min, 11 mL of a 1 M solution of Dibal in toluene. The mixture is stirred an additional 6 minutes, and is then quenched by addition of 2 mL of methanol. The cold bath is removed and 20 mL of a Rochelle salt solution is added and vigorously stirred while the mixture warms to ambient temperature. The product is extracted into ether and the organic phase is washed successively with Rochelle salt solution, water, and brine. It is dried over Na2SO4, concentrated, and chromatographed over silica gel, eluting with 50% ethyl acetate in heptane, to afford the title compound as a colorless oil (0.79 g, 2.3 mmol, 52%). 1H NMR (CDCl3) δ 9.7 (s, 1H), 7.85 (m, 1H), 7.79 (s, 1H), 7.49 (m, 2H), 6.81 (d, J=7 Hz, 1H), 4.78 (m, 1H), 3.46 (br t, 2H), 3.15 (br t, 2H), 1.82 (m, 2H), 1.70 (m, 2H), 1.62-1.53 (m, 3H), 1.01 (m, 9H), 0.75 (br t, 3H).

Workup

  1. additionTo this is added, dropwise over 5 min
  2. customis then quenched by addition of 2 mL of methanol
  3. customThe cold bath is removed
  4. addition20 mL of a Rochelle salt solution is added
  5. stirringvigorously stirred while the mixture
  6. customwarms to ambient temperature
  7. extractionThe product is extracted into ether
  8. washthe organic phase is washed successively with Rochelle salt solution, water, and brine
  9. dry with materialIt is dried over Na2SO4
  10. concentrationconcentrated
  11. customchromatographed over silica gel
  12. washeluting with 50% ethyl acetate in heptane

Sources & evidence

ORD record
ord-1a3aaafe4bac4fd887f35b6ec8a1cdad
Source dataset
uspto-grants-2005_11
Patent number
US06962934B2

Reaction notes

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