2,6-Dimethoxybenzoyl chloride → (3S-trans)-3-[(2,6-dimethoxybenzoyl)amino]-4-methyl-1-[(phenylmethyl)oxy]-2-azetidinone

HRID 484681

반응식

HRID 484681 반응식
[NH2:1][C@H:2]1[C@H:5]([CH3:6])[N:4]([O:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:3]1=[O:15].C1(C)C(S([O-])(=O)=O)=CC=CC=1.[CH3:27][O:28][C:29]1[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[C:30]=1[C:31](Cl)=[O:32]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:39][O:38][C:34]1[CH:35]=[CH:36][CH:37]=[C:29]([O:28][CH3:27])[C:30]=1[C:31]([NH:1][C@H:2]1[C@H:5]([CH3:6])[N:4]([O:7][CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:3]1=[O:15])=[O:32]

참가 물질

6

반응물 3

HCID 748102,6-Dimethoxybenzoyl chlorideHCID 3424274ToluenesulfonateHCID 13036842(3S-trans)-3-amino-4-methyl-1-(phenylmethoxy)-2-azetidinone

생성물 1

HCID 13036849(3S-trans)-3-[(2,6-dimethoxybenzoyl)amino]-4-methyl-1-[(phenylmethyl)oxy]-2-azetidinone

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

To a cold (-10° C.) solution of (3S-trans)-3-amino-4-methyl-1-(phenylmethoxy)-2-azetidinone, toluenesulfonate (0.95 g; see example 2D) in methylene chloride (50 ml) is added 2,6-dimethoxybenzoyl chloride (0.60 g) and 4-dimethylaminopyridine (0.61 g). The reaction is stirred under nitrogen and allowed to rise to 26° C. over five hours. The reaction mixture is concentrated to an oil and partitioned between ethyl acetate and aqueous hydrogen sulfate solution. The organic layer is washed with aqueous sodium bicarbonate, and brine, dried over sodium sulfate and concentrated to a foam (0.848 g).

후처리

  1. concentrationThe reaction mixture is concentrated to an oil
  2. custompartitioned between ethyl acetate and aqueous hydrogen sulfate solution
  3. washThe organic layer is washed with aqueous sodium bicarbonate, and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to a foam (0.848 g)

출처 및 근거

ORD 기록
ord-b3c4aefaa8124d5eaa3567e0899a03f9
출처 데이터셋
uspto-grants-1985_08
특허 번호
US04533660

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