(3S,4R)-4-amino-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrile → (3S,4R)-4-amino-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrile

HRID 704773

반응식

HRID 704773 반응식
[NH2:1][C@@H:2]1[C:7]2[CH:8]=[C:9]([C:12]#[N:13])[CH:10]=[CH:11][C:6]=2[O:5][C:4]([CH3:15])([CH3:14])[C@H:3]1[OH:16].O.[C:18]1([CH3:45])[CH:23]=[CH:22][C:21]([C:24]([C@@:26]([C:42]([OH:44])=[O:43])([OH:41])[C@@:27]([C:32]([C:34]2[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=2)=[O:33])([OH:31])[C:28]([OH:30])=[O:29])=[O:25])=[CH:20][CH:19]=1>C(O)C>[C:18]1([CH3:45])[CH:23]=[CH:22][C:21]([C:24]([C@@:26]([C:42]([OH:44])=[O:43])([OH:41])[C@@:27]([C:32]([C:34]2[CH:35]=[CH:36][C:37]([CH3:40])=[CH:38][CH:39]=2)=[O:33])([OH:31])[C:28]([OH:30])=[O:29])=[O:25])=[CH:20][CH:19]=1.[NH2:1][C@@H:2]1[C:7]2[CH:8]=[C:9]([C:12]#[N:13])[CH:10]=[CH:11][C:6]=2[O:5][C:4]([CH3:14])([CH3:15])[C@H:3]1[OH:16]

참가 물질

5

반응물 2

HCID 10943936(3S,4R)-4-amino-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrileHCID 69630779HCID 69630779, 화합물

생성물 2

HCID 10943936(3S,4R)-4-amino-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrile수율 22.3%HCID 29414711Di-para-toluoyl-L-tartaric acid

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of trans-4-amino-3,4-dihydro-2,2-dimethyl-3-hydroxy-2H-1-benzopyran-6-carbonitrile (193 g) and (-)-di-p-toluoyl-L-tartaric acid monohydrate (358 g) was dissolved in ethanol (600 ml) under reflux. The mixture was cooled to room temperature and stood for 3 days to give a white precipitate. This precipitate was collected by filtration, washed with a small volume of ethanol, and recrystallized twice from ethanol to give (-)-di-p-toluoyl-L-tartaric acid salt of (3S,4R)-4-amino-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (43.1 g).

후처리

  1. temperatureunder reflux
  2. customto give a white precipitate
  3. filtrationThis precipitate was collected by filtration
  4. washwashed with a small volume of ethanol
  5. customrecrystallized twice from ethanol

출처 및 근거

ORD 기록
ord-a9fa8379fc7944f0968f5a2d06b0cb30
출처 데이터셋
uspto-grants-1991_01
특허 번호
US04988723

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