Water → N-(1-cyclohexyl methyl-2-pyrrolidinyl-methyl)-2-methoxy-4-amino-5-ethylsulphonyl-benzamide

HRID 652769ノート

反応式

HRID 652769 の反応式
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([NH2:12])[C:9]([S:13]([CH2:16][CH3:17])(=[O:15])=[O:14])=[CH:8][C:4]=1[C:5]([OH:7])=O.O.Cl[C:20](OCC)=O.[CH:25]1([N:31]2[CH2:35][CH2:34][CH2:33][C:32]2(C)[CH2:36][NH2:37])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>C(N(CC)CC)C.CC(C)=O>[CH:25]1([N:31]2[CH2:35][CH2:34][CH2:33][CH:32]2[CH:36]([CH3:20])[NH:37][C:5](=[O:7])[C:4]2[CH:8]=[C:9]([S:13]([CH2:16][CH3:17])(=[O:15])=[O:14])[C:10]([NH2:12])=[CH:11][C:3]=2[O:2][CH3:1])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1

参加物

7

反応物 4

HCID 962WaterHCID 10928Ethyl chloroformateHCID 30182324-Amino-5-(ethylsulphonyl)-o-anisic acidHCID 212685261-Cyclohexyl-methyl-2-aminomethyl pyrrolidine

生成物 1

HCID 86741587N-(1-cyclohexyl methyl-2-pyrrolidinyl-methyl)-2-methoxy-4-amino-5-ethylsulphonyl-benzamide

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 8471Triethylamine溶媒

反応条件

温度
0 °C

実験手順

25.9 g of 2-methoxy-4-amino-5-ethylsulphonyl benzoic acid, 40 ml of water, 200 ml of acetone and 13.9 ml of triethylamine (density 0.726) are placed in a 500 ml flask fitted with an agitator, a thermometer and a dropping funnel. The solution is cooled to about 0° to 5° C. and 10.9 g of ethyl chloroformate is dripped in. The mixture is agitated for 40 minutes at about 0° C., then 19.6 g of 1-cyclohexyl-methyl-2-aminomethyl pyrrolidine is added drop by drop. The mixture is agitated for 2 hours at room temperature then left to stand. The acetone is evaporated under vacuum and the residue is dissolved in 100 ml of water and 25 ml of acetic acid and filtered in the presence of vegetable black. The filtrate is made alkaline with 100 ml of 40% soda lye. A precipitate is formed; this is filtered, washed with plenty of water and dissolved moist in 230 ml of boiling acetone. The hot solution is filtered in the presence of vegetable black and the filtrate is crystallised. The product is drained, washed with a little acetone and dried in an oven at 50° C.

後処理

  1. customfitted with an agitator
  2. temperatureThe solution is cooled to about 0° to 5° C.
  3. stirringThe mixture is agitated for 2 hours at room temperature
  4. waitthen left
  5. customThe acetone is evaporated under vacuum
  6. dissolutionthe residue is dissolved in 100 ml of water
  7. filtration25 ml of acetic acid and filtered in the presence of vegetable black
  8. customA precipitate is formed
  9. filtrationthis is filtered
  10. washwashed with plenty of water
  11. dissolutiondissolved moist in 230 ml of boiling acetone
  12. filtrationThe hot solution is filtered in the presence of vegetable black
  13. customthe filtrate is crystallised
  14. washwashed with a little acetone
  15. customdried in an oven at 50° C.

出典と根拠

ORDレコード
ord-b995a7d26ac44833b37ac282f87436e7
出典データセット
uspto-grants-1987_06
特許番号
US04673686

反応ノート

読み込み中…