HCID 69201240, compound → HCID 69201297, compound

HRID 2377661Notes

Reaction equation

HRID 2377661 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:11]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]([O:22]C(C)(C)C)=[O:21])=[CH:14][CH:13]=3)[CH:10]([CH2:27][CH2:28][O:29][C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)[C:9]2=[O:37])=[CH:4][CH:3]=1>C(O)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:11]([C:12]3[CH:13]=[CH:14][C:15]([O:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:16][CH:17]=3)[CH:10]([CH2:27][CH2:28][O:29][C:30]3[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=3)[C:9]2=[O:37])=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 69201240HCID 69201240, compound

Product 1

HCID 69201297HCID 69201297, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 1-(4-fluorophenyl)-3-[2-(4-fluorophenoxy)ethyl]-4-[4-(t-butoxycarbonylmethoxy)phenyl]azetidin-2-one (Method 7; 1.045 g, 2.05.1 mmol) in formic acid (4 ml) was stirred at room temperature for 22 hours. The solvent was removed under reduced pressure and the residue was dissolved in DCM (10 ml). The organic layer was successively washed with a saturated solution of sodium hydrogen carbonate (aq; 5 ml), water (5 ml) and brine (5 ml), dried and concentrated to give the title compound as a white solid (0.941 g; ˜quantitative yield). NMR (400 MHz) 2.25-2.45 (m, 2H), 3.20-3.30 (m, 1H), 4.00-4.20 (m, 2H), 4.65 (s, 2H), 4.80 (d, 1H), 6.75-6.80 (m, 2H), 6.85-7.00 (m, 6H), 7.20-7.30 (m, 4H); m/z: 454.0.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in DCM (10 ml)
  3. washThe organic layer was successively washed with a saturated solution of sodium hydrogen carbonate (aq; 5 ml), water (5 ml) and brine (5 ml)
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ffec8bd076154b50ae9fc56e0309c56c
Source dataset
uspto-grants-2008_12
Patent number
US07470678B2

Reaction notes

Loading…