Hydrochloric Acid → HCID 564973, compound

HRID 2111526Notes

Reaction equation

HRID 2111526 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.C([O:14][C:15]([N:17]1CC(=O)[CH2:18]1)=[O:16])(C)(C)C.O.Cl.[CH2:24]1[CH2:28]O[CH2:26][CH2:25]1>>[CH3:28][CH2:24][CH2:25][CH2:26][N:17]([C:15]([O:16][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:14])[CH3:18]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 178418676HCID 178418676, compound

Product 1

HCID 564973HCID 564973, compoundYield 70%

Conditions

Temperature
0 °C

Procedure

4-Fluorophenyl magnesium bromide (6.0 mL, 1.0 solution in THF, 6 mmol) was added dropwise to a solution of 3-oxo-azetidine-1-carboxylic acid t-butyl ester (514 mg, 3 mmol) in THF (10 mL) at 0° C. The reaction mixture was stirred at 0° C. for one hour. Water was added, and the mixture was acidified with 1 N HCl solution and then extracted with ether (2×30 mL). The organic layers were combined, dried (MgSO4) and concentrated to give a light yellow oil. This material was fractionated using preparative. HPLC. Homogeneous fractions were combined and concentrated to give the intermediate carbamate a colorless oil, (564 mg, 70% yield).

Workup

  1. extractionextracted with ether (2×30 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customto give a light yellow oil
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-aa118bcc04ce418f8948662bc6926c03
Source dataset
uspto-grants-2009_04
Patent number
US07521442B2

Reaction notes

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