4-Methylmorpholine → N-[[trans 3-(acetylthiomethyl)-2-oxo-1-aza-cyclodecan-10-yl]-carbonyl]-trans 4-hydroxy-L-proline ethyl ester

HRID 5403

반응식

HRID 5403 반응식
[C:1]([S:4][CH2:5][C@H:6]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]([C:16]([OH:18])=O)[NH:8][C:7]1=[O:19])(=[O:3])[CH3:2].ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.[CH2:38]([O:40][C:41](=[O:48])[C@@H:42]1[CH2:46][C@@H:45]([OH:47])[CH2:44][NH:43]1)[CH3:39].Cl.CN(CCCN=C=NCC)C>C(Cl)Cl>[CH2:38]([O:40][C:41](=[O:48])[C@@H:42]1[CH2:46][C@@H:45]([OH:47])[CH2:44][N:43]1[C:16]([C@@H:9]1[NH:8][C:7](=[O:19])[C@@H:6]([CH2:5][S:4][C:1](=[O:3])[CH3:2])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:18])[CH3:39]

참가 물질

7

반응물 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12709304Ethyl trans-4-hydroxy-L-prolinate hydrochlorideHCID 86747202trans 3-(Acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxylic acid

생성물 1

HCID 86747211N-[[trans 3-(acetylthiomethyl)-2-oxo-1-aza-cyclodecan-10-yl]-carbonyl]-trans 4-hydroxy-L-proline ethyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

The enantiomer of trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxylic acid of Example 16(0.23 g, 0.80 mmol), 1-hydroxybenzotriazole (0.11 g, 0.80 mmol), 4-methylmorpholine (0.22 mL, 2.0 mmol), and L-hydroxyproline ethyl ester hydrochloride (0.16 g, 0.80 mmol) are dissolved in methylene chloride (5.0 mL), and the reaction is cooled to 0° C. To this solution is added N-[dimethylaminopropyl]-N'-ethylcarbodiimide hydrochloride (0.31 g, 1.60 mmol), and the reaction is allowed to warm up to room temperature and stirred overnight. The reaction is diluted with more methylene chloride, and the organic layer is washed with 1N hydrochloric acid, saturated sodium bicarbonate, dried (MgSO4), and the solvent is evaporated. The product is purified by silica gel chromatography (80% ethyl acetate/hexane) to give N-[[trans 3-(acetylthiomethyl)-2-oxo-1-aza-cyclodecan-10-yl]-carbonyl]-trans 4-hydroxy-L-proline ethyl ester as a single enantiomer, [α]D +5.73° (c=4.1 mg/ml, CH2Cl2) which is assigned the 3R, 10S configuration.

후처리

  1. temperatureto warm up to room temperature
  2. washthe organic layer is washed with 1N hydrochloric acid, saturated sodium bicarbonate
  3. dry with materialdried (MgSO4)
  4. customthe solvent is evaporated
  5. customThe product is purified by silica gel chromatography (80% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-cd1d5c5dc1cf4e4bb0fa6676330d839a
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05244889

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