Lithium hydroxide, monohydrate → HCID 18957360, compound

HRID 2379549Notes

Reaction equation

HRID 2379549 reaction equation
[C:1]([N:4]([CH2:17][C:18]1[O:19][C:20]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:22]=1)[C:5]1[CH:6]=[C:7]([CH:14]=[CH:15][CH:16]=1)[O:8][CH2:9][C:10]([O:12]C)=[O:11])(=[O:3])[CH3:2].O[Li].O>CO>[C:1]([N:4]([CH2:17][C:18]1[O:19][C:20]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:21]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:22]=1)[C:5]1[CH:6]=[C:7]([CH:14]=[CH:15][CH:16]=1)[O:8][CH2:9][C:10]([OH:12])=[O:11])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrate2×HCID 54409140HCID 54409140, compound

Product 1

HCID 18957360HCID 18957360, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl [3-[N-acetyl-[(4,5-diphenyl-2-oxazolyl)methyl]amino]phenoxy]acetate (0.58 g, 1.3 mmol), LiOH.H2O (0.05 g, 1.3 mmol) and MeOH (30 mL) was stirred at room temperature for about 15 hours before adding LiOH.H2O (0.05 g, 1.3 mmol). After about 1 hour, the solvent was evaporated, the residue diluted with 1N HC1 solution and extracted with CH2Cl2. The combined extracts were washed with saturated NaCl solution, dried over MgSO4 and concentrated in vacuo to leave [3-[N-acetyl-[(4,5-diphenyl-2-oxazolyl) methyl]amino]phenoxy]acetic acid (0.51 g, 91%), mp 75-80° C. IR (KBr) 2500 (CO2H), 1740 (CO2H), 1660 (NCOCH3) cm-1 ; 1H NMR (CDCl3) δ1.95 (3H, s, COCH3), 4.55 (2H, s, OCH2), 5.11 (2H, s, NCH2) 6.70-6.95 (3H, m, aromatic H) , 7.25-7.40 (7H, m, aromatic H) , 7.45-7.65 (4H, m, aromatic H); MS m/z 443 (MH+).

Workup

  1. waitAfter about 1 hour
  2. customthe solvent was evaporated
  3. additionthe residue diluted with 1N HC1 solution
  4. extractionextracted with CH2Cl2
  5. washThe combined extracts were washed with saturated NaCl solution
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5d91161722be4eebaee310c3a2373de4
Source dataset
uspto-grants-1994_11
Patent number
US05362879

Reaction notes

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