(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-carbamoyl-3-methyl-5,6-dihydropyridine-1(2H)-carboxylate → (2S,5R)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-3-methyl-1,2,5,6-tetrahydropyridine-2-carboxamide

HRID 627129

반응식

HRID 627129 반응식
[CH2:1]([O:4][N:5]([C@H:18]1[CH2:23][N:22](C(OC(C)(C)C)=O)[C@H:21]([C:31](=[O:33])[NH2:32])[C:20]([CH3:34])=[CH:19]1)[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3]>ClCCl.[Br-].[Zn+2].[Br-]>[CH2:1]([O:4][N:5]([C@H:18]1[CH2:23][NH:22][C@H:21]([C:31]([NH2:32])=[O:33])[C:20]([CH3:34])=[CH:19]1)[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3]

참가 물질

4

반응물 1

HCID 89852450(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-carbamoyl-3-methyl-5,6-dihydropyridine-1(2H)-carboxylate2회

생성물 1

HCID 89852088(2S,5R)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-3-methyl-1,2,5,6-tetrahydropyridine-2-carboxamide수율 91%

시약·촉매·용매 2

HCID 10421208Zinc bromide촉매HCID 6344Dichloromethane용매2회

실험 절차

(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-carbamoyl-3-methyl-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 83, 2.785 g, 5.61 mmol) and zinc(II) bromide (2.53 g, 11.22 mmol) was added DCM (10 mL) and stirred at rt overnight. The reaction mixture was diluted with dichloromethane and washed with saturated sodium bicarbonate and brine. The organics were dried over magnesium sulfate, filtered and concentrated to afford the desired product (2.015 g, 91%) as a beige foam.

후처리

  1. washwashed with saturated sodium bicarbonate and brine
  2. dry with materialThe organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-bb8cd7d1b8094c849b4cf50c21b64855
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309245B2

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