Dicyclohexylcarbodiimide → N-[2-(4,6-Dimethoxypyrimidin-2-yl)acetyl]-2-methoxycarbonylbenzylsulfonamid

HRID 344581ノート

反応式

HRID 344581 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([CH2:11][C:12]([OH:14])=O)[N:4]=1.C1(N=C=NC2CCCCC2)CCCCC1.[CH3:30][O:31][C:32]([C:34]1[CH:44]=[CH:43][CH:42]=[CH:41][C:35]=1[CH2:36][S:37]([NH2:40])(=[O:39])=[O:38])=[O:33]>ClCCl.CN(C)C1C=CN=CC=1>[CH3:10][O:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[N:4]=[C:5]([CH2:11][C:12]([NH:40][S:37]([CH2:36][C:35]2[CH:41]=[CH:42][CH:43]=[CH:44][C:34]=2[C:32]([O:31][CH3:30])=[O:33])(=[O:38])=[O:39])=[O:14])[N:6]=1

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 124207552-(4,6-Dimethoxypyrimidin-2-yl)acetic acidHCID 13958774Benzoic acid, 2-[(aminosulfonyl)methyl]-, methyl ester

生成物 1

HCID 14580665N-[2-(4,6-Dimethoxypyrimidin-2-yl)acetyl]-2-methoxycarbonylbenzylsulfonamid

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 1.9 g of (4,6-dimethoxypyrimidin-2-yl)acetic acid in 40 ml of absolute dichloromethane is added dropwise at 0° C. to 2° C. to a solution of 1.9 g of dicyclohexylcarbodiimide, 100 mg of 4-dimethylaminopyridine and 2.1 g of 2-methoxycarbonylbenzylsulfonamide in 40 ml of absolute dichloromethane. Stirring is continued for 1 hour at 0° C., and the mixture is allowed to come to room temperature and stirred for another 0.5 hour. The solids are filtered off, and the filtrate is concentrated in a rotary evaporator. 100 ml of 2 N sodium carbonate solution are added to the residue, the mixture is stirred for 0.5 hour at room temperature, and the solids are filtered off with suction. The sodium carbonate alkaline phase is extracted twice using diethyl ether, and a pH of 2-3 is established using concentrated hydrochloric acid. Stirring is continued for 15 minutes, the solids are filtered off with suction, the filter residue is washed once with water and twice with ether, and dried in vacuo. This gives 2.4 g of N-[2-(4,6-dimethoxypyrimidin-2-yl)acetyl]-2-methoxycarbonylbenzylsulfonamide of melting point 98°-101° C.

後処理

  1. customto come to room temperature
  2. stirringstirred for another 0.5 hour
  3. filtrationThe solids are filtered off
  4. concentrationthe filtrate is concentrated in a rotary evaporator
  5. addition100 ml of 2 N sodium carbonate solution are added to the residue
  6. stirringthe mixture is stirred for 0.5 hour at room temperature
  7. filtrationthe solids are filtered off with suction
  8. extractionThe sodium carbonate alkaline phase is extracted twice using diethyl ether
  9. stirringStirring
  10. waitis continued for 15 minutes
  11. filtrationthe solids are filtered off with suction
  12. washthe filter residue is washed once with water and twice with ether
  13. customdried in vacuo

出典と根拠

ORDレコード
ord-5948eeb5f41145369882c9a1481ba0a4
出典データセット
uspto-grants-1991_10
特許番号
US05053072

反応ノート

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