HCID 18682370, compound → 3-(3-Isobutyl-2-oxo-4-{[4-(3-o-tolyl-ureido)-phenyl]-acetyl}-piperazin-1-yl)-butyric acid

HRID 277184Notes

Reaction equation

HRID 277184 reaction equation
C[O:2][C:3](=[O:38])[CH2:4][CH:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13](=[O:32])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[CH3:31])=[O:23])=[CH:17][CH:16]=2)[CH:9]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:8]1=[O:37])[CH3:6]>[OH-].[Na+].C(O)(C)(C)C>[CH2:33]([CH:9]1[N:10]([C:13](=[O:32])[CH2:14][C:15]2[CH:16]=[CH:17][C:18]([NH:21][C:22]([NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[CH3:31])=[O:23])=[CH:19][CH:20]=2)[CH2:11][CH2:12][N:7]([CH:5]([CH3:6])[CH2:4][C:3]([OH:38])=[O:2])[C:8]1=[O:37])[CH:34]([CH3:36])[CH3:35]

Participants

4

Reactant 1

HCID 18682370HCID 18682370, compound

Product 1

HCID 183138573-(3-Isobutyl-2-oxo-4-{[4-(3-o-tolyl-ureido)-phenyl]-acetyl}-piperazin-1-yl)-butyric acidYield 82.8%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 3-(3-isobutyl-2-oxo-4-{[4-(3-o-tolyl-ureido)-phenyl]-acetyl}-piperazin-1-yl)-butyric acid methyl ester (20 mg, 0.038 mmol) in a mixture of 1 ml of 0.1 N NaOH and 1 ml of tert-butanol was stirred for 16 hrs at room temperature. The reaction mixture was then concentrated under reduced pressure, dissolved in water (5 ml) and extracted with ether (5 ml×2). The aqueous portion was then acidified to pH<3 with 1N HCl and extracted with ethyl acetate. The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give 16 mg of the title compound as a yellow sticky oil. MS [M+1]+509.3; 1H nmr (400 MHz, CD3OD) δ0.88-1.70 (m, 12H), 2.25 (s, 3H), 2.34-4.96 (m, 10H), 6.98 (t, J=7.4 Hz, 1H), 7.11-7.40 (m, 6H), 7.59 (d, J=7.5 Hz, 1).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. dissolutiondissolved in water (5 ml)
  3. extractionextracted with ether (5 ml×2)
  4. extractionextracted with ethyl acetate
  5. washThe combined organics were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-33ef61efbbaf4a7f8239e5d50b6899b1
Source dataset
uspto-grants-2002_03
Patent number
US06355662B1

Reaction notes

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