1,1'-Carbonyldiimidazole → N-tert-butyloxycarbonyl-4-(4-amino-5-chloro-2-methoxyphenylcarbonylaminomethyl)piperidine

HRID 1250527ノート

反応式

HRID 1250527 の反応式
C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:13][C:14]1[C:22]([Cl:23])=[CH:21][C:17]([C:18]([OH:20])=O)=[C:16]([O:24][CH3:25])[CH:15]=1.[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36]([CH2:39][NH2:40])[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27]>CN(C)C=O>[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36]([CH2:39][NH:40][C:18]([C:17]2[CH:21]=[C:22]([Cl:23])[C:14]([NH2:13])=[CH:15][C:16]=2[O:24][CH3:25])=[O:20])[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27]

参加物

5

反応物 3

HCID 682631,1'-CarbonyldiimidazoleHCID 816264-Amino-5-chloro-2-methoxybenzoic acidHCID 7368171-Boc-4-(aminomethyl)piperidine

生成物 1

HCID 11200348N-tert-butyloxycarbonyl-4-(4-amino-5-chloro-2-methoxyphenylcarbonylaminomethyl)piperidine収率 80%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

1,1′-Carbonyldiimidazole (1.61 g, 9.91 mmol) was added to a solution of 4-amino-5-chloro-2-methoxybenzoic acid (2.0 g, 9.91 mmol) in dimethylformamide (5 ml). After stirring for 5 min. at room temperature, solution of N-tert-butyloxycarbonyl-4-(aminomethyl)piperidine (1.77 g, 8.26 mmol) in dimethylformamide (5 ml) was added and the reaction mixture was heated at 55° C. After 23 h, the product was extracted into ethyl acetate and the organic layer was washed with aqueous sodium bicarbonate, dried over magnesium sulfate, filtered and concentrated. Flash chromatography of the crude product with 2:1, ethyl acetate/hexanes as the eluant gave N-tert-butyloxycarbonyl-4-(4-amino-5-chloro-2-methoxyphenylcarbonylaminomethyl)piperidine (2.63 g) as a foam.

後処理

  1. temperaturethe reaction mixture was heated at 55° C
  2. waitAfter 23 h
  3. extractionthe product was extracted into ethyl acetate
  4. washthe organic layer was washed with aqueous sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-8e6454ef3b76456db8399c360256109e
出典データセット
uspto-grants-2002_01
特許番号
US06339087B1

反応ノート

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