Methanol → HCID 18957362, compound

HRID 2379551Notes

Reaction equation

HRID 2379551 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][N:19]([C:32]([O:34][CH3:35])=[O:33])[C:20]3[CH:21]=[C:22]([CH:29]=[CH:30][CH:31]=3)[O:23][CH2:24][C:25]([O:27]C)=[O:26])[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O[Li].O.CO>O>[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][N:19]([C:32]([O:34][CH3:35])=[O:33])[C:20]3[CH:21]=[C:22]([CH:29]=[CH:30][CH:31]=3)[O:23][CH2:24][C:25]([OH:27])=[O:26])[O:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 54321190HCID 54321190, compound

Product 1

HCID 18957362HCID 18957362, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl [3-[[(4,5-diphenyl-2-oxazolyl)methyl](methoxycarbonyl) amino]phenoxy]acetate (4.16 g, 9 mmol), LiOH.H2O (0.56 g, 13 mmol), MeOH (45 mL) and H2O (15 mL) was stirred at room temperature for about 3 hours. The solvent was removed in vacuo, the residue diluted with H2O and 2N HCl until pH=2 and a yellow solid filtered off. Recrystallization from a mixture of CH2Cl2 and hexanes gave [3-[[(4,5-diphenyl-2-oxazolyl)methyl](methoxycarbonyl)amino]phenoxy]acetic acid (2.25 g, 55%), mp 153-155° C. IR (KBr) 2700-2500 (CO2H), 1750 (NCO2CH3), 1710 (CO2H) cm-1 ; 1H NMR (CDCl3) δ3.68 (3H, s, NCO2CH3), 4.51 (2H, s, OCH2CO2H), 4.60 (1H, bs, CO2H), 4.95 (2H, s, CH2 -oxazole), 6.77 (1H, dd, J=9 Hz, J'=2 Hz, aromatic H), 6.94 (2H, m, aromatic H), 7.15 to 7.40 (7H, m, aromatic H), 7.45 to 7.65 (4H, m, aromatic H); MS m/z 459 (MH+).

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue diluted with H2O and 2N HCl until pH=2
  3. filtrationa yellow solid filtered off
  4. customRecrystallization
  5. additionfrom a mixture of CH2Cl2 and hexanes

Sources & evidence

ORD record
ord-9eab9fd02a654b3fb7526cfb7fbb2dee
Source dataset
uspto-grants-1994_11
Patent number
US05362879

Reaction notes

Loading…