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

HRID 430687

반응식

HRID 430687 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b31a7c863d644f85b0bd55bceeb15496
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06323223B1

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