Hydrochloric Acid → 3-[3-Benzyloxy-3-(4-fluoro-phenyl)-propyl]-4-(4-benzyloxy-phenyl)-1-(4-fluoro-phenyl)-azetidin-2-one

HRID 1052897

Reaction equation

HRID 1052897 reaction equation
C[O:2][C:3](=O)[CH:4]([CH:23]([C:32]1[CH:37]=[CH:36][C:35]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[CH:34][CH:33]=1)[NH:24][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)[CH2:5][CH2:6]C(OCC1C=CC=CC=1)C1C=CC(F)=CC=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Cl.[C:58]([O:61][CH2:62][CH3:63])(=O)[CH3:59]>O1CCCC1>[CH2:62]([O:61][CH:58]([C:59]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)[CH2:6][CH2:5][CH:4]1[CH:23]([C:32]2[CH:33]=[CH:34][C:35]([O:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[CH:36][CH:37]=2)[N:24]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[C:3]1=[O:2])[C:63]1[CH:6]=[CH:5][CH:4]=[CH:23][CH:32]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 2733832Lithium HexamethyldisilazideHCID 667134205-Benzyloxy-2-[(4-benzyloxy-phenyl)-(4-fluoro-phenylamino)-methyl]-5-(4-fluoro-phenyl)-pentanoic acid methyl ester

Product 1

HCID 667132803-[3-Benzyloxy-3-(4-fluoro-phenyl)-propyl]-4-(4-benzyloxy-phenyl)-1-(4-fluoro-phenyl)-azetidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-22.5 °C

Procedure

10 gms of 5-Benzyloxy-2-[(4-benzyloxy-phenyl)-(4-fluoro-phenylamino)-methyl]-5-(4-fluoro-phenyl)-pentanoic acid methyl ester was dissolved in 500 ml of tetrahydrofuran and cool the reaction mass to −20 to −25° C. To the reaction mass 16 ml of 1M Lithium bis(trimethylsilyl)amide was added under nitrogen atmosphere and stirred for about 30 minutes. To the reaction mass 100 ml of 2 N hydrochloride solution was added at 20-25° C. Stirred the reaction mass by adding 150 ml of ethyl acetate and separated the organic layer. Washed the organic layer with water and dried over sodium sulphate. Distilled the solvent completely under reduced pressure at 50-55° C. to get 8.0 gms of 3-[3-Benzyloxy-3-(4-fluoro-phenyl)-propyl]-4-(4-benzyloxy-phenyl)-1-(4-fluoro-phenyl)-azetidin-2-one.

Workup

  1. stirringStirred the reaction mass
  2. customseparated the organic layer
  3. washWashed the organic layer with water
  4. dry with materialdried over sodium sulphate
  5. distillationDistilled the solvent completely under reduced pressure at 50-55° C.

Sources & evidence

ORD record
ord-b92fb61efef34c0f9d8b1e1b477d5ec4
Source dataset
uspto-grants-2016_07
Patent number
US09388440B2

Linked notes

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