Acetone → HCID 22063465, Verbindung

HRID 1827763Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1827763
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:20](=[O:26])[CH:21](OCC)O)[C:12]2[O:17][CH2:16][C:15](=[O:18])[NH:14][C:13]=2[CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:27]([O:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][C:37]([NH2:40])([CH3:39])[CH3:38])=[CH:32][CH:31]=1)[CH3:28].[BH4-].[Na+].CC(C)=O>C(O)C.C(O)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:20]([OH:26])[CH2:21][NH:40][C:37]([CH3:38])([CH3:39])[CH2:36][C:33]2[CH:34]=[CH:35][C:30]([O:29][CH2:27][CH3:28])=[CH:31][CH:32]=2)[C:12]2[O:17][CH2:16][C:15](=[O:18])[NH:14][C:13]=2[CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 22063474HCID 22063474, VerbindungHCID 22063492HCID 22063492, Verbindung

Produkt 1

HCID 22063465HCID 22063465, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

2.14 g (6.0 mmol) of 6-benzyloxy-8-(2-ethoxy-2-hydroxyacetyl)-4H-benzo[1,4]oxazin-3-one and 1.0 g (5.2 mmol) of 2-(4-ethoxyphenyl)-1,1-dimethylethylamine are stirred in 40 mL ethanol for one hour at 50° C.–80° C. After cooling to ambient temperature, 0.23 g (6.0 mmol) of sodium borohydride are added and the mixture is stirred for a further hour. The reaction mixture is combined with 5 mL acetone, stirred for 30 minutes, acidified with glacial acetic acid, and evaporated down. The residue is combined with water and ethyl acetate and made alkaline. The organic phase is separated off, washed with water, dried with sodium sulfate, and freed from solvent in vacuo. The residue is dissolved again in ethyl acetate and water, combined with concentrated hydrochloric acid, and diluted with diethyl ether. The solid precipitated is suction filtered and washed with diethyl ether. White solid. Yield: 2.0 g (61%, hydrochloride); melting point: 214° C.–216° C.

Aufarbeitung

  1. stirringstirred for 30 minutes
  2. customevaporated down
  3. customThe organic phase is separated off
  4. washwashed with water
  5. dry with materialdried with sodium sulfate
  6. dissolutionThe residue is dissolved again in ethyl acetate
  7. additiondiluted with diethyl ether
  8. customThe solid precipitated
  9. filtrationfiltered
  10. washwashed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-54965bd16611420580bf095b0c70443b
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07056916B2

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