Lithium hydroxide, monohydrate → HCID 18957366, compound

HRID 2379553Notes

Reaction equation

HRID 2379553 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][N:19]([C:32]([O:34][CH2:35][CH3:36])=[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>CCO>[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][N:19]([C:32]([O:34][CH2:35][CH3:36])=[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

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 9935116HCID 9935116, compound

Product 1

HCID 18957366HCID 18957366, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl [3-[[(4,5-diphenyl-2-oxazolyl) methyl](ethoxycarbonyl)amino]phenoxy]acetate (0.90 g, 1.9 mmol), LiOH.H2O (82 mg, 2 mmol) and 95% EtOH (25 mL) was stirred at room temperature for about 25 hours. The EtOH was evaporated, the residue diluted with H2O and acidified with 2N HCl solution. Extraction with CH2Cl2 afforded an oil which was chromatographed first on a column of silica gel using CH2Cl2 /MeOH (9:1) as eluent and subsequently on a column of silica gel using hexanes/EtOAc/AcOH (12:7:1) as eluent to give [3-[[(4,5-diphenyl-2-oxazolyl) methyl](ethoxycarbonyl)amino]phenoxy]acetic acid (0.70 g, 80%). IR (film) 3000, 1710 cm-1 ; 1H NMR (CDCl3) δ1.22 (3H, t, J=8 Hz, OCH2CH3), 4.21 (2H, q, J=8 Hz, OCH2CH 3), 4.55 (2H, s, OCH2CO2CH3), 5.03 (2H, s, CH2 -oxazole), 6.79 (1H, dd, J=9 Hz, J'=2 Hz, aromatic H), 7.00 (2H, m, aromatic H), 7.20 to 7.40 (7H, m, aromatic H), 7.50 to 7.70 (4H, m, aromatic H), 10.49 (1H, bs, CO2H); MS m/z 473 (MH+).

Workup

  1. customThe EtOH was evaporated
  2. additionthe residue diluted with H2O
  3. extractionExtraction with CH2Cl2
  4. customafforded an oil which
  5. customwas chromatographed first on a column of silica gel

Sources & evidence

ORD record
ord-6be2819906324bc991527b47b66a95bd
Source dataset
uspto-grants-1994_11
Patent number
US05362879

Reaction notes

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