Hydrochloric Acid → (3S,7S,8R,9S)-7-benzyl-8-isobutoxy-9-methyl-2-oxo-1,5-dioxonan-3-aminium chloride

HRID 75739노트

반응식

HRID 75739 반응식
[CH2:1]([C@@H:8]1[C@@H:16]([O:17][CH2:18][CH:19]([CH3:21])[CH3:20])[C@H:15]([CH3:22])[O:14][C:13](=[O:23])[C@@H:12]([N:24](C(OC(C)(C)C)=O)C(=O)OC(C)(C)C)[CH2:11][O:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:39]>C(Cl)Cl>[Cl-:39].[CH2:1]([C@@H:8]1[C@@H:16]([O:17][CH2:18][CH:19]([CH3:20])[CH3:21])[C@H:15]([CH3:22])[O:14][C:13](=[O:23])[C@@H:12]([NH3+:24])[CH2:11][O:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 86701230tert-butyl N-[(3S,7S,8R,9S)-7-benzyl-8-isobutoxy-9-methyl-2-oxo-1,5-dioxonan-3-yl]-N-tert-butoxycarbonylcarbamate

생성물 1

HCID 86701231(3S,7S,8R,9S)-7-benzyl-8-isobutoxy-9-methyl-2-oxo-1,5-dioxonan-3-aminium chloride

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of tert-butyl N-[(3S,7S,8R,9S)-7-benzyl-8-isobutoxy-9-methyl-2-oxo-1,5-dioxonan-3-yl]-N-tert-butoxycarbonylcarbamate (3.586 g, 6.69 mmol) in CH2Cl2 (33 mL) was added HCl (4M in dioxane; 33.5 ml, 134 mmol, 20 equiv). This solution was stirred for 1 h and concentrated to furnish (3S,7S,8R,9S)-7-benzyl-8-isobutoxy-9-methyl-2-oxo-1,5-dioxonan-3-aminium chloride as a white solid. The solid was suspended in CH2Cl2 (66 mL), and N-methylmorpholine (4.42 ml, 40.2 mmol, 6.00 equiv) was added, causing dissolution of the solid. To this solution were added 3-hydroxy-4-methoxypicolinic acid (1.70 g, 10.0 mmol, 1.50 equiv) and HATU (4.07 g, 10.71 mmol, 1.60 equiv). The resulting suspension was stirred at room temperature for 20 h, concentrated, and purified by automated silica gel column chromatography (2-12% acetone in CH2Cl2) to yield N-((3S,7S,8R,9S)-7-benzyl-8-isobutoxy-9-methyl-2-oxo-1,5-dioxonan-3-yl)-3-hydroxy-4-methoxypicolinamide (2.08 g, 63.9%) as a yellow oil.

후처리

  1. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3166d465312742969fd5e8da89035f15
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835462B2

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