Potassium Hydroxide → (+)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(N-benzyloxycarbonyl-N-methylamino)ethyl]-8-methyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

HRID 1981935ノート

反応式

HRID 1981935 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:15]([OH:16])[C:14](=[O:17])[NH:13][C:12]3[CH:18]=[CH:19][C:20]([CH3:22])=[CH:21][C:11]=3[S:10]2)=[CH:5][CH:4]=1.[OH-].[K+].[CH2:25]([O:32][C:33]([N:35]([CH2:37][CH2:38]Cl)[CH3:36])=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CS(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:15]([OH:16])[C:14](=[O:17])[N:13]([CH2:38][CH2:37][N:35]([C:33]([O:32][CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[O:34])[CH3:36])[C:12]3[CH:18]=[CH:19][C:20]([CH3:22])=[CH:21][C:11]=3[S:10]2)=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 14797Potassium HydroxideHCID 10358332HCID 10358332、化合物HCID 13592063Benzyl (2-chloroethyl)methylcarbamate

生成物 1

HCID 70467950(+)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(N-benzyloxycarbonyl-N-methylamino)ethyl]-8-methyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one収率 91.8%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒2 回

反応条件

温度
50 °C

実験手順

A mixture of 2 g of (±)-cis-2-(4-methoxyphenyl)-3-hydroxy- 8-methyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, 0.42 g of powdered potassium hydroxide and 15 ml of dimethylsulfoxide is stirred at 50° C. for 30 minutes. A solution of 2.64 g of 2-(N-benzyloxycarbonyl-N-methylamino)ethyl chloride in 5 ml of dimethylsulfoxide is added to the mixture, and the mixture is stirred at 50° C. for 3 days. The mixture is poured into ice-water, and the aqueous mixture is extracted with ethyl acetate. The extract is washed with a saturated sodium chloride solution, dried and evaporated under reduced pressure to remove solvent. The residue is purified by silica gel chromatography (solvent, chloroform: ethyl acetate=10:1). 2.95 g of (+)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(N-benzyloxycarbonyl-N-methylamino)ethyl]-8-methyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one are obtained as an oil.

後処理

  1. stirringthe mixture is stirred at 50° C. for 3 days
  2. extractionthe aqueous mixture is extracted with ethyl acetate
  3. washThe extract is washed with a saturated sodium chloride solution
  4. customdried
  5. customevaporated under reduced pressure
  6. customto remove solvent
  7. customThe residue is purified by silica gel chromatography (solvent, chloroform: ethyl acetate=10:1)

出典と根拠

ORDレコード
ord-714051114a62466294d80a2bba860537
出典データセット
uspto-grants-1986_06
特許番号
US04594342

反応ノート

読み込み中…