Water → HCID 18957369, compound

HRID 2379556Notes

Reaction equation

HRID 2379556 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH:18]3[CH2:22][CH2:21][C:20](=[O:23])[N:19]3[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([O:33]C)=[O:32])[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.O>CO.C(Cl)(Cl)Cl>[C:1]1([C:7]2[N:8]=[C:9]([CH:18]3[CH2:22][CH2:21][C:20](=[O:23])[N:19]3[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])[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

Participants

6

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 18957361HCID 18957361, compound

Product 1

HCID 18957369HCID 18957369, compoundYield 50.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6212ChloroformSolvent

Procedure

A mixture of methyl 2- (4,5-diphenyl-2-oxazolyl)-5-oxo-l-pyrrolidineoctanoate (3.60 g, 7.8 mmol) , LiOH.H2O (986 mg, 24 mmol), MeOH (60 mL) and H2O (10 mL) was stirred at room temperature. After about 45 minutes, the mixture was concentrated, diluted with 1N HCl solution and extracted with CH2Cl2. The combined extracts were dried over Na2SO4 and concentrated to leave an oil. Chromatography on a column of silica gel using a mixture of MeOH and CHCl3 (1:1) as eluent furnished 2-(4,5-diphenyl-2-oxazolyl) -5-oxo-1-pyrrolidineoctanoic acid (1.76 g, 50%). IR (Film) 3600-2400 (CO2H), 1725 (CO2H), 1695 (N.CO) cm-1 ; 1H NMR (CDCl3) δ1.20-1.65 (10H, m, CH2), 2.24 (2H, t, J=7.5 Hz, CH2CO2H), 2.30- 2.60 (3H, m, CH2 of ring), 2.75 (1H, m, CH2 of ring), 3.03 (1H, m, NCH2 of side chain), 3.60 (1H, quintuplet, J=7 Hz, NCH2 of side chain), 4.90 (1H, m, NCH of ring), 5.26 (0.3H, s, CH2Cl2), 7.30-7.45 (6H, m, aromatic H), 7.50-7.65 (4H, m, aromatic H), 9.87 (1H, bs, CO2H); MS m/z 447 (MH+).

Workup

  1. concentrationthe mixture was concentrated
  2. additiondiluted with 1N HCl solution
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined extracts were dried over Na2SO4
  5. concentrationconcentrated
  6. customto leave an oil

Sources & evidence

ORD record
ord-726a8918598942fab89a1d564344bc6d
Source dataset
uspto-grants-1994_11
Patent number
US05362879

Reaction notes

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