3-[3-(3-Methyl-1-{2-[4-(3-o-tolyl-ureido)-phenyl]-acetylamino}-butyl)-isoxazol-5-yl]-propionic acid methyl ester → 3-[3-(3-Methyl-1-{2-[4-(3-o-tolyl-ureido)-phenyl]-acetylamino}-butyl)-isoxazol-5-yl]-propionic acid

HRID 277187Notes

Reaction equation

HRID 277187 reaction equation
C[O:2][C:3](=[O:37])[CH2:4][CH2:5][C:6]1[O:10][N:9]=[C:8]([CH:11]([NH:16][C:17](=[O:36])[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([NH:25][C:26]([NH:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[CH3:35])=[O:27])=[CH:21][CH:20]=2)[CH2:12][CH:13]([CH3:15])[CH3:14])[CH:7]=1>C(O)(C)(C)C.[OH-].[Na+]>[CH3:14][CH:13]([CH3:15])[CH2:12][CH:11]([C:8]1[CH:7]=[C:6]([CH2:5][CH2:4][C:3]([OH:37])=[O:2])[O:10][N:9]=1)[NH:16][C:17](=[O:36])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH3:35])=[O:27])=[CH:21][CH:20]=1

Participants

4

Reactant 1

HCID 186823683-[3-(3-Methyl-1-{2-[4-(3-o-tolyl-ureido)-phenyl]-acetylamino}-butyl)-isoxazol-5-yl]-propionic acid methyl ester

Product 1

HCID 99354073-[3-(3-Methyl-1-{2-[4-(3-o-tolyl-ureido)-phenyl]-acetylamino}-butyl)-isoxazol-5-yl]-propionic acid

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 3-[3-(3-methyl-1-{2-[4-(3-o-tolyl-ureido)-phenyl]-acetylamino}-butyl)-isoxazol-5-yl]-propionic acid methyl ester (17 mg) in tert-BuOH (1 ml) and 0.1 N NaOH (1 ml) was stirred at room temperature. After 20 h the mixture was concentrated under reduced pressure, dissolved in water (5 ml) and extracted with EtOAc (5 ml×3). The aqueous layer was then acidified to pH 3 with IN HCl and extracted with EtOAc. The combined organics were washed with brine; dried over Na2SO4; filtered and concentrated under reduced pressure to give the title compound as a white amorphous solid. MP=?; MS [M+1]+493.2; 1H nmr (400 MHz, CD3OD) δ0.87 (d, 3H), 0.91 (d, 3H), 1.53-1.66 (m, 3H), 2.26 (s, 3H), 2.64 (t, J=7.4 Hz, 2H), 2.97 (t, J=7.5 Hz, 2H), 3.44 (s, 2H), 5.08 (m, 1H), 6.00 (s, 1H), 6.99 (t, 1H), 7.11-7.36 (m, 6H), 7.59 (d, J=7.9 Hz,1H).

Workup

  1. concentrationAfter 20 h the mixture was concentrated under reduced pressure
  2. dissolutiondissolved in water (5 ml)
  3. extractionextracted with EtOAc (5 ml×3)
  4. extractionextracted with EtOAc
  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-7362f37f1d5044c8be8f582759a814fa
Source dataset
uspto-grants-2002_03
Patent number
US06355662B1

Reaction notes

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