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

HRID 484681

反応式

HRID 484681 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-b3c4aefaa8124d5eaa3567e0899a03f9
出典データセット
uspto-grants-1985_08
特許番号
US04533660

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