HCID 69201094, compound → HCID 69199496, compound

HRID 2377665Notes

Reaction equation

HRID 2377665 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][S: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:7]=[CH:6][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][S:29][C:30]3[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=3)[C:9]2=[O:37])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 69201094HCID 69201094, compound

Product 1

HCID 69199496HCID 69199496, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 1-(4-fluorophenyl)-3-[2-(4-fluorophenylthio)ethyl]-4-[4-(t-butoxycarbonylmethoxy)phenyl]azetidin-2-one (Method 16; 0.880 g, 1.67 mmol) in formic acid (5 ml) was stirred at room temperature for 19 hours. The solvent was removed under reduced pressure and the residue was dissolved in DCM (25 ml). The organic layer was washed twice with water (1×10 ml and 1×5 ml) and once with brine (5 ml), dried over magnesium sulphate and concentrated. This gave the title compound as a colourless oil (0.800 g; ˜quantitative yield). NMR (CD3COOD, 400 MHz) 2.10-2.30 (m, 2H), 3.10 (dt, 2H), 3.30-3.40 (m, 1H), 4.75 (s, 2H), 4.80 (d, 1H), 6.95-7.05 (m, 6H), 7.25-7.40 (m, 6H); m/z: 470.2.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in DCM (25 ml)
  3. washThe organic layer was washed twice with water (1×10 ml and 1×5 ml) and once with brine (5 ml)
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8c8511536f43444784bcbac4fe3f84af
Source dataset
uspto-grants-2008_12
Patent number
US07470678B2

Reaction notes

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