Hydrochloric Acid → 2-(2-Formamidothiazol-4-yl)-2-(2-tert-butoxycarbonylaminoethoxyimino)acetic acid

HRID 255749Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 255749
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH2:15][CH2:16][NH2:17])[C:10]([OH:12])=[O:11])[N:8]=1)=[O:2].C(=O)(O)[O-].[Na+].Cl.C1(C(=N[O:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=O)C#N)C=CC=CC=1>O.O1CCCC1.C(N(CC)CC)C>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH2:15][CH2:16][NH:17][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:34])[C:10]([OH:12])=[O:11])[N:8]=1)=[O:2]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 516892Sodium BicarbonateHCID 543766712-(2-Aminoethoxyimino)-2-(2-formamidothiazol-4-yl)acetic acid

Produkt 1

HCID 540828852-(2-Formamidothiazol-4-yl)-2-(2-tert-butoxycarbonylaminoethoxyimino)acetic acidAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of 2-(2-formamidothiazol-4-yl)-2-(2-aminoethoxyimino)acetic acid (syn isomer, 0.80 g.) and triethylamine (0.45 g.), in a solution of a saturated aqueous solution of sodium bicarbonate (4 ml.), tetrahydrofuran (35 ml.) and water (25 ml.) was adjusted to pH 8.5 with hydrochloric acid. 2-Phenyl-2-(tert-butoxycarbonyloxyimino)acetonitrile (0.77 g.) was added to the stirred solution and stirred at room temperature for 3 hours. After distilling off tetrahydrofuran from the resultant solution, the aqueous solution was washed with diethyl ether, and adjusted to pH 1.5 with 85% phosphoric acid. The solution was extracted with ethyl acetate (50 ml.), and the extract was washed with a saturated aqueous solution of sodium chloride (10 ml.), dried over magnesium sulfate and concentrated under reduced pressure to give 2-(2-formamidothiazol-4-yl)-2-(2-tert-butoxycarbonylaminoethoxyimino)acetic acid (syn isomer, 0.40 g.).

Aufarbeitung

  1. distillationAfter distilling off tetrahydrofuran from the resultant solution
  2. washthe aqueous solution was washed with diethyl ether
  3. extractionThe solution was extracted with ethyl acetate (50 ml.)
  4. washthe extract was washed with a saturated aqueous solution of sodium chloride (10 ml.)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-37fd78a4d11f4f47909d365a6e03a51d
Quelldatensatz
uspto-grants-1987_10
Patentnummer
US04698337

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