1-Hydroxybenzotriazole → N-tert-butyloxycarbonyl-4-(4-amino-5-chloro-2-methoxyphenylcarbonylaminomethyl)piperidine

HRID 344234노트

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HRID 344234 반응식
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.[NH2:16][C:17]1[C:25]([Cl:26])=[CH:24][C:20]([C:21](O)=[O:22])=[C:19]([O:27][CH3:28])[CH:18]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O>[NH2:16][C:17]1[C:25]([Cl:26])=[CH:24][C:20]([C:21]([NH:1][CH2:2][CH:3]2[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]2)=[O:22])=[C:19]([O:27][CH3:28])[CH:18]=1

참가 물질

6

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 816264-Amino-5-chloro-2-methoxybenzoic acidHCID 7368171-Boc-4-(aminomethyl)piperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

생성물 1

HCID 11200348N-tert-butyloxycarbonyl-4-(4-amino-5-chloro-2-methoxyphenylcarbonylaminomethyl)piperidine수율 102.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

4-Aminomethyl-1-tert-butoxycarbonylpiperidine (10.0 g) was dissolved in dimethylformamide and 4-amino-5-chloro-2-methoxybenzoic acid (9.4 g) and 1-hydroxybenzotriazole (6.6 g) were added. After stirring at 0° C. for 40 min, 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (9.4 g) was added, and the mixture was stirred at room temperature for 24 hr. The reaction mixture was concentrated under reduced pressure. Aqueous potassium carbonate solution was added to the residue and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography to give 19.0 g of 4-amino-5-chloro-N-(1-tert-butoxycarbonylpiperidin-4-ylmethyl)-2-methoxybenzamide.

후처리

  1. stirringthe mixture was stirred at room temperature for 24 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionAqueous potassium carbonate solution was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe extract was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-4d5cf63f151740218c19feb15d6535b2
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05864039

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