HCID 12627440, compound → HCID 23593510, compound

HRID 2243639Notes

Reaction equation

HRID 2243639 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([N:9]2[CH:12]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[CH:11]([CH2:21][CH2:22][CH:23]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[OH:24])[C:10]2=[O:32])[CH:6]=[CH:7][CH:8]=1.[C:33]([O:36][CH:37]([CH:53]([O:57][C:58](=[O:60])[CH3:59])[C:54](Cl)=[O:55])[CH:38]([O:49][C:50](=[O:52])[CH3:51])[CH:39]([O:45][C:46](=[O:48])[CH3:47])[CH2:40][O:41][C:42](=[O:44])[CH3:43])(=[O:35])[CH3:34]>C(Cl)Cl.C(N(CC)CC)C.C(OCC)(=O)C>[C:58]([O:57][CH:53]([C:54](=[O:55])[NH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N:9]2[C:10](=[O:32])[CH:11]([CH2:21][CH2:22][CH:23]([C:25]3[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=3)[OH:24])[CH:12]2[C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)[CH:4]=1)[CH:37]([O:36][C:33](=[O:35])[CH3:34])[CH:38]([O:49][C:50](=[O:52])[CH3:51])[CH:39]([O:45][C:46](=[O:48])[CH3:47])[CH2:40][O:41][C:42](=[O:44])[CH3:43])(=[O:60])[CH3:59]

Participants

6

Reactant 2

HCID 12627440HCID 12627440, compoundHCID 22252078HCID 22252078, compound

Product 1

HCID 23593510HCID 23593510, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

112 mg (0.24 mmol) of 1-(3-aminomethylphenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-methoxyphenyl)azetidin-2-one are dissolved in 5 ml of methylene chloride and 0.5 ml of triethylamine. At 0° C., 0.5 g of 2,3,4-triacetoxy-1-(acetoxychlorocarbonylmethyl)butyl acetate are added, and the mixture is allowed to thaw to room temperature. After 30 minutes, the mixture is diluted with ethyl acetate and then filtered through silica gel. The solvent is distilled off and the residue is purified by flash chromatography. The product is obtained as an amorphous solid: C42H47FN2O4 (822.84) MS (ESI): M+=823.3.

Workup

  1. customthaw to room temperature
  2. filtrationfiltered through silica gel
  3. distillationThe solvent is distilled off
  4. customthe residue is purified by flash chromatography
  5. customThe product is obtained as an amorphous solid

Sources & evidence

ORD record
ord-8c0ad64d9ad9490091c6775832bd9c63
Source dataset
uspto-grants-2010_03
Patent number
US07674773B2

Reaction notes

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