反応 #46334

反応方程式

triethylamine

dimethyl sulfoxide

1-{(R*)-(4-chlorophenyl)[4-(methoxycarbonyl)-phenyl]methyl}azetidin-3-ol

oxalyl chloride

→

1-{(R*)-(4-chlorophenyl)[4-(methoxycarbonyl)phenyl]methyl}azetidin-3-one

収率 83.4%

溶媒

water

dichloromethane

dichloromethane

反応条件

後処理

1. 1
   その他1-{(R*)-(4-Chlorophenyl)[4-methoxycarbonyl)-phenyl]methyl}azetidin-3-one, A isomer form, may be prepared
2. 2
   workup.STIRRINGAfter stirring for 3 hours at −60° C.
3. 3
   その他to return to 0° C
4. 4
   workup.STIRRINGthe mixture is stirred
5. 5
   その他separated
6. 6
   乾燥The organic phase is dried over magnesium sulfate
7. 7
   ろ過filtered
8. 8
   濃縮concentrated to dryness at 50° C. under reduced pressure (2.7 kPa)
9. 9
   その他The orange-colored oil obtained
10. 10
    その他is chromatographed on a silica gel column (particle size 0.06-0.200 mm, diameter 2 cm, height 30 cm), under an argon pressure of 0.5 bar
11. 11
    洗浄eluting with a cyclohexane and ethyl acetate (75/25 by volume) mixture
12. 12
    その他collecting 30-cm3 fractions
13. 13
    濃縮concentrated to dryness under reduced pressure (2.7 kPa)

実験手順

1-{(R*)-(4-Chlorophenyl)[4-methoxycarbonyl)-phenyl]methyl}azetidin-3-one, A isomer form, may be prepared by carrying out the procedure in the following manner: 0.90 cm3 of dimethyl sulfoxide is poured over 10 minutes into a solution, cooled to −60° C., of 0.55 cm3 of oxalyl chloride in 5 cm3 of dichloromethane. After stirring for 30 minutes at −60° C., a solution of 1.75 g of 1-{(R*)-(4-chlorophenyl)[4-(methoxycarbonyl)-phenyl]methyl}azetidin-3-ol, A isomer form, in 20 cm3 of dichloromethane is added to the mixture over 15 minutes. After stirring for 3 hours at −60° C., 2.7 cm3 of triethylamine are poured in and then the reaction medium is allowed to return to 0° C. 20 cm3 of water are then added, the mixture is stirred and then separated after settling. The organic phase is dried over magnesium sulfate, filtered and then concentrated to dryness at 50° C. under reduced pressure (2.7 kPa). The orange-colored oil obtained is chromatographed on a silica gel column (particle size 0.06-0.200 mm, diameter 2 cm, height 30 cm), under an argon pressure of 0.5 bar, eluting with a cyclohexane and ethyl acetate (75/25 by volume) mixture and collecting 30-cm3 fractions. Fractions 2 to 15 are combined and then concentrated to dryness under reduced pressure (2.7 kPa). 1.45 g of 1-{(R*)-(4-chlorophenyl)[4-(methoxycarbonyl)phenyl]methyl}azetidin-3-one, A isomer form, are obtained in the form of a yellow foam.

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