4-Methylmorpholine → 2-(2-Oxo-2-phenyl-ethylcarbamoyl)-piperidine-1-carboxylic acid benzyl ester

HRID 1823932노트

반응식

HRID 1823932 반응식
[C:1]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]1[C:17]([OH:19])=O)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].Cl.[NH2:21][CH2:22][C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:24].O[N:32]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[N:34]=N1.CN(C)CCCCN=C=NCC.CN1CCOCC1>ClCCl.O>[C:25]1([C:23]2[N:34]=[C:35]([CH:40]3[CH2:39][CH2:38][CH2:37][CH2:36][NH:32]3)[NH:21][CH:22]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[CH2:4]([O:3][C:1]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[C:17](=[O:19])[NH:21][CH2:22][C:23](=[O:24])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:2])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

참가 물질

9

반응물 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 688345(S)-1-N-Cbz-Pipecolinic acidHCID 2723597Ethanone, 2-amino-1-phenyl-, hydrochloride (1:1)HCID 21914090(4-Dimethylamino-butyl)-ethyl-carbodiimide

생성물 2

HCID 235707182-(2-Oxo-2-phenyl-ethylcarbamoyl)-piperidine-1-carboxylic acid benzyl esterHCID 178420113HCID 178420113, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

(S)-1-(Carbobenzyloxy)-2-piperidinecarboxylic acid (15.8 g, 60 mmol), 2-amino-1phenyl-ethanone hydrochloride (10.30 g, 60 mmol), and HOBT (1-hydroxybenzo-triazole) (16.20 g, 120 mmol) were mixed in dichloromethane (400 mL). The stirring mixture was cooled to 0° C. and then (4-dimethylamino-butyl)-ethyl-carbodiimide (14.90 g, 78 mmol) and NMM (N-methyl-morpholine) (7.27 g, 72 mmol) were added. The reaction mixture was then warmed to room temperature. After 16 hours the reaction mixture was treated with water, and the resulting solid was filtered. The organic phase from the filtrate was separated and washed consecutively with saturated NaHCO3, 2N citric acid, and saturated NaHCO3 once again, then dried over MgSO4, filtered, and concentrated to yield the title product 2-(2-oxo-2-phenyl-ethylcarbamoyl)-piperidine-1-carboxylic acid benzyl ester as a yellow oil, which was used without further purification.

후처리

  1. temperatureThe reaction mixture was then warmed to room temperature
  2. filtrationthe resulting solid was filtered
  3. customThe organic phase from the filtrate was separated
  4. washwashed consecutively with saturated NaHCO3, 2N citric acid, and saturated NaHCO3 once again
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-adeb1121502a4c3eba558bee447a4e46
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07041681B2

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