(3S,4R)-4-amino-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrile → HCID 14511095, Verbindung

HRID 704774

Reaktionsgleichung

Reaktionsgleichung von HRID 704774
[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].[C:17]1([CH3:44])[CH:22]=[CH:21][C:20]([C:23]([C@:25]([C:41]([OH:43])=[O:42])([OH:40])[C@:26]([C:31]([C:33]2[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=2)=[O:32])([OH:30])[C:27]([OH:29])=[O:28])=[O:24])=[CH:19][CH:18]=1>C(O)C>[C:17]1([CH3:44])[CH:22]=[CH:21][C:20]([C:23]([C@:25]([C:41]([OH:43])=[O:42])([OH:40])[C@:26]([C:31]([C:33]2[CH:34]=[CH:35][C:36]([CH3:39])=[CH:37][CH:38]=2)=[O:32])([OH:30])[C:27]([OH:29])=[O:28])=[O:24])=[CH:19][CH:18]=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]

Komponenten

5

Edukt 2

HCID 10943936(3S,4R)-4-amino-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrileHCID 22860073(2R,3R)-2,3-dihydroxy-2,3-bis(4-methylbenzoyl)butanedioic acid

Produkt 2

HCID 14511095HCID 14511095, VerbindungAusbeute 58,7 %HCID 22860073(2R,3R)-2,3-dihydroxy-2,3-bis(4-methylbenzoyl)butanedioic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of trans-4-amino-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (32.74 g) and (+)-di-p-toluoyl-D-tartaric acid (57.95 g) was dissolved in ethanol (85 ml) under reflux. The mixture was cooled to room temperature and stood for 4 days to give a white precipitate. This precipitate was collected by filtration, washed with a mixture of ethanol and diisopropyl ether (100 ml, 1:2), and recrystallized from ethanol (80 ml) to give (+)-di-p-toluoyl-D-tartaric acid salt of (3R,4S)-4-amino-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (19.20 g).

Aufarbeitung

  1. temperatureunder reflux
  2. customto give a white precipitate
  3. filtrationThis precipitate was collected by filtration
  4. washwashed with a mixture of ethanol and diisopropyl ether (100 ml, 1:2)
  5. customrecrystallized from ethanol (80 ml)

Quellen und Nachweise

ORD-Eintrag
ord-81d6b01d2c2a468ca4c5f8cdc5e0bd14
Quelldatensatz
uspto-grants-1991_01
Patentnummer
US04988723

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