Sodium borohydride → Ethyl 2-hydroxy-2-(2-mesylamino-1,3-thiazol-4-yl)acetate

HRID 325373Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 325373
[S:1]([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[O:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:10]=1)([CH3:4])(=[O:3])=[O:2].[BH4-].[Na+]>C(O)C>[OH:17][CH:11]([C:9]1[N:10]=[C:6]([NH:5][S:1]([CH3:4])(=[O:2])=[O:3])[S:7][CH:8]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Komponenten

5

Edukt 3

HCID 4311764Sodium borohydrideHCID 19978726Ethyl 2-(2-mesylamino-1,3-thiazol-4-yl)glyoxylateHCID 178473045HCID 178473045, Verbindung

Produkt 1

HCID 20254378Ethyl 2-hydroxy-2-(2-mesylamino-1,3-thiazol-4-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a mixture of ethyl 2-(2-mesylamino-1,3-thiazol-4-yl)glyoxylate, which can be represented as ethyl 2-(2-mesylimino-2,3-dihydro-1,3-thiazol-4-yl)glyoxylate, (3.60 g.) and ethanol (50 ml.) was added sodium borohydride (0.32 g.) under stirring and ice-cooling, and then the mixture was stirred for 40 minutes at room temperature. After the reaction, the reaction mixture was concentrated. The residue was poured into a mixture of ethyl acetate (100 ml.) and dilute hydrochloric acid, and the aqueous solution was separated. Thus obtained aqueous solution (pH 1 to 2) was subjected to salting-out and then extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The extract was treated with activated charcoal and then the solvent was distilled off to give a solid of ethyl 2-hydroxy-2-(2-mesylamino-1,3-thiazol-4-yl)acetate, which can be represented as ethyl 2-hydroxy-2-(2-mesylimino-2,3-dihydro-1,3-thiazol-4-yl)acetate, (2.6 g.)

Aufarbeitung

  1. temperatureice-cooling
  2. stirringthe mixture was stirred for 40 minutes at room temperature
  3. customAfter the reaction
  4. concentrationthe reaction mixture was concentrated
  5. additionThe residue was poured into a mixture of ethyl acetate (100 ml.) and dilute hydrochloric acid
  6. customthe aqueous solution was separated
  7. extractionextracted with ethyl acetate
  8. washThe extract was washed with a saturated aqueous solution of sodium chloride
  9. dry with materialdried over magnesium sulfate
  10. additionThe extract was treated with activated charcoal
  11. distillationthe solvent was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-061f6d166a1a469e8efbc409a76cbd4c
Quelldatensatz
uspto-grants-1984_04
Patentnummer
US04440766

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