Hydrochloric Acid → 3-Hydroxy-1-(4-methoxycarbonyl-1,3-oxazol-2-yl)azetidine

HRID 891804Notes

Reaction equation

HRID 891804 reaction equation
C([O:9][CH:10]1[CH2:13][N:12]([C:14]2[O:15][CH:16]=[C:17]([C:19]([O:21][CH3:22])=[O:20])[N:18]=2)[CH2:11]1)(=O)C1C=CC=CC=1.C[O-].[Na+].Cl>CO.C(Cl)Cl.O1CCOCC1>[OH:9][CH:10]1[CH2:13][N:12]([C:14]2[O:15][CH:16]=[C:17]([C:19]([O:21][CH3:22])=[O:20])[N:18]=2)[CH2:11]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 222428453-Benzoyloxy-1-(4-methoxycarbonyl-1,3-oxazol-2-yl)azetidine

Product 1

HCID 222430383-Hydroxy-1-(4-methoxycarbonyl-1,3-oxazol-2-yl)azetidineYield 77.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-benzoyloxy-1-(4-methoxycarbonyl-1,3-oxazol-2-yl)azetidine (5.24 g, 17.3 mmol) (obtained as described in Reference Example 70(6)) in a mixture of methanol (260 ml) and methylene chloride (80 ml) was added a catalytic amount of sodium methoxide at room temperature and the mixture was stirred for 1 hour. After checking the completion of the reaction, the mixture was neutralized with 4 N hydrogen chloride gas in dioxane and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using methylene chloride:methanol (95:5) as the eluant to afford 3-hydroxy-1-(4-methoxycarbonyl-1,3-oxazol-2-yl)azetidine (2.65 g, yield 77%) as pale brown crystals.

Workup

  1. customthe completion of the reaction
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-44fae9d07fb546a48fb59f7c161dc105
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

Loading…