Ethyl oxoacetate → (3R-trans)-[(6-Cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4yl)amino]acetic acid, ethyl ester

HRID 356672Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 356672
[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]([O:21][CH2:22][CH3:23])(=[O:20])[CH:18]=O.C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>CO.C(O)(=O)C>[C:12]([C:9]1[CH:10]=[CH:11][C:6]2[O:5][C:4]([CH3:14])([CH3:15])[C@H:3]([OH:16])[C@@H:2]([NH:1][CH2:18][C:17]([O:21][CH2:22][CH3:23])=[O:20])[C:7]=2[CH:8]=1)#[N:13]

Komponenten

7

Edukt 4

HCID 70211Ethyl oxoacetateHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 14511095(3R,4S)-4-amino-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

Produkt 1

HCID 10756893(3R-trans)-[(6-Cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4yl)amino]acetic acid, ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of (3R-trans)-4-amino-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (the title A compound) and ethyl glyoxylate (2.5 g) in methanol (30 mL) and acetic acid (2 mL) at 0° C. under argon atmosphere was added sodium cyanoborohydride (1.5 g). The reaction mixture was stirred at 0 C. for 30 minutes, poured into saturated sodium bicarbonate (150 mL) and extracted with ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated. The residue was purified by chromatography to give an oil, which solidified upon standing (1.8 g, 48%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography
  5. customto give an oil, which

Quellen und Nachweise

ORD-Eintrag
ord-2c67c7dc40684817bfea479c176dc261
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05837702

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