Hydrochloric Acid → HCID 69830687, compound

HRID 1584309Notes

Reaction equation

HRID 1584309 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]([CH2:25][CH2:26][CH2:27][CH:28]2[O:32][C:31](=[O:33])[NH:30][C:29]2=[O:34])[CH:8]=[CH:9][C:10]=1[O:11][CH2:12][C:13]1[N:14]=[C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:16][C:17]=1[CH3:18])(C)C.Cl>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[OH:4][C:5]1[CH:6]=[C:7]([CH2:25][CH2:26][CH2:27][CH:28]2[O:32][C:31](=[O:33])[NH:30][C:29]2=[O:34])[CH:8]=[CH:9][C:10]=1[O:11][CH2:12][C:13]1[N:14]=[C:15]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[O:16][C:17]=1[CH3:18]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69831316HCID 69831316, compound

Product 1

HCID 69830687HCID 69830687, compoundYield 34.6%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of titanium tetrachloride (TiCl4) (1.1 g) in dichloromethane (5 ml) was added dropwise, at 0° C., to a solution of 5-[3-[3-isopropoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]propyl]-2,4-oxazolidinedione (0.7 g) in dichloromethane (25 ml). The mixture was stirred for one hour at room temperature. The reaction mixture was poured over 2N HCl, which was stirred for 15 minutes at room temperature. The organic layer was separated, and the aqueous layer was subjected to extraction with chloroform. The organic layer combined was and successively washed with water, 2N HCl and water, which was dried (MgSO4) and concentrated. The concentrate was subjected to column chromatography on silica gel. From the fraction eluted with chloroform-methanol (50:1), was obtained 5-[3-[3-hydroxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]propyl]-2,4-oxazolidinedione (0.22 g, 34%), which was recrystallized from chloroform-methanol to give colorless prisms, m.p.162-164° C.

Workup

  1. stirringwas stirred for 15 minutes at room temperature
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was subjected to extraction with chloroform
  4. washsuccessively washed with water, 2N HCl and water, which
  5. dry with materialwas dried (MgSO4)
  6. concentrationconcentrated
  7. washFrom the fraction eluted with chloroform-methanol (50:1)

Sources & evidence

ORD record
ord-65c79fbde06e4d2fb343d773f7289886
Source dataset
uspto-grants-1999_08
Patent number
US05932601

Reaction notes

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