Dimethyl Sulfoxide → (R*)-(4-[chlorophenyl)[4-(methoxycarbonyl)phenyl]methyl}azetidin-3-one
Reaction equation
ClC1C=CC([C@@H:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:16][CH:15]=2)[N:9]2[CH2:12][C:11](=[O:13])[CH2:10]2)=CC=1.[C:24](Cl)(=O)[C:25](Cl)=O.Cl[CH2:31][Cl:32].[CH3:33]S(C)=O.C(N([CH2:42][CH3:43])CC)C>>[Cl:32][C:31]1[CH:25]=[CH:24][CH:43]=[CH:42][C:33]=1[C@:17]1([C:20]([O:22][CH3:23])=[O:21])[CH:16]=[CH:15][C:14]([CH2:8][N:9]2[CH2:10][C:11](=[O:13])[CH2:12]2)=[CH:19][CH2:18]1Participants
Procedure
1-{(R*)-(4-chlorophenyl)[4-(methoxycarbonyl)phenyl]methyl}azetidin-3-one, form B isomer, may be prepared by carrying out the operation as described in Example 40, starting with 8.7 cm3 of oxalyl chloride, 350 cm3 of dichloromethane, 14.2 cm3 of dimethyl sulfoxide, 29.0 g of 1-{(R*)-(4-chlorophenyl)[4-(methoxycarbonyl)phenyl]methyl}azetidin-3-ole, form B isomer, and 43 cm3 of triethylamine. The crude product is chromatographed on a silica gel column (particle size 0.06-0.200 mm, diameter 4 cm, height 40 cm), eluting with dichloromethane and collecting 250 cm3 fractions. Fractions 7 to 25 are combined and then concentrated to dryness under reduced pressure (2.7 kPa). 15.5 g of 1-{(R*)-(4-[chlorophenyl)[4-(methoxycarbonyl)phenyl]methyl}azetidin-3-one, form B isomer, are obtained in the form of an orange-colored oil.
Workup
- customThe crude product is chromatographed on a silica gel column (particle size 0.06-0.200 mm, diameter 4 cm, height 40 cm)
- washeluting with dichloromethane
- customcollecting 250 cm3 fractions
- concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
Sources & evidence
- ORD record
- ord-949b859f12c74f9ca8197c4dba5118b7
- Source dataset
- uspto-grants-2005_02
- Patent number
- US06858603B2
Reaction notes
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