Pyridine → 4-[6-(4-Nitro-phenoxycarbonyloxy)-hexylcarbamoyloxy]-piperidine-1-carboxylic acid 4-phenoxyphenyl ester

HRID 618288ノート

反応式

HRID 618288 の反応式
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([N:17]2[CH2:22][CH2:21][CH:20]([O:23][C:24]([NH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][OH:33])=[O:25])[CH2:19][CH2:18]2)=[O:16])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:41]([O:43][C:44]1[CH:49]=[CH:48][C:47]([N+:50]([O-:52])=[O:51])=[CH:46][CH:45]=1)=[O:42]>C(Cl)Cl>[O:1]([C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([N:17]2[CH2:22][CH2:21][CH:20]([O:23][C:24](=[O:25])[NH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][C:41]([O:43][C:44]3[CH:45]=[CH:46][C:47]([N+:50]([O-:52])=[O:51])=[CH:48][CH:49]=3)=[O:42])[CH2:19][CH2:18]2)=[O:16])=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 537895824-[[[(6-Hydroxyhexyl)amino]-carbonyl]oxy]-1-piperidinecarboxylic acid 4-phenoxyphenyl ester

生成物 1

HCID 542367634-[6-(4-Nitro-phenoxycarbonyloxy)-hexylcarbamoyloxy]-piperidine-1-carboxylic acid 4-phenoxyphenyl ester収率 100.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of the alcohol (40.0 g, 88 mmol) produced in Example 4 and pyridine (7.1 ml, 88 mmol) in 300 ml of methylene chloride was added under nitrogen dropwise over one hour to a solution of 4-nitrophenyl chloroformate (17.7 g, 88 mmol) in 300 ml of methylene chloride at ice bath temperature. The reaction was stirred at ice bath temperature for two hours and overnight at room temperature. The reaction was extracted one time with 1N HCl, multiple times with saturated Na2CO3, dried (MgSO4) and the solvent removed under reduced pressure to give 54.9 g of an off-white solid. Recrystallization from 1:1 ethyl acetatehexane gave 51.6 g (95%) of the title compound as a white crystalline solid, mp 117-120° C.

後処理

  1. customovernight
  2. customat room temperature
  3. extractionThe reaction was extracted one time with 1N HCl, multiple times with saturated Na2CO3
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed under reduced pressure

出典と根拠

ORDレコード
ord-802a19b88eea45a6a9e78983f4d34ed8
出典データセット
uspto-grants-1999_09
特許番号
US05952354

反応ノート

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