Sodium Hydroxide → (3RS)-3-{5-[2-(2-o-Tolylamino-benzoxazol-6-yl)-acetylamino]-pyrid-2-yl}-butyric acid

HRID 49697Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 49697
C([O:3][C:4](=[O:35])[CH2:5][CH:6]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:34])[CH2:16][C:17]2[CH:33]=[CH:32][C:20]3[N:21]=[C:22]([NH:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[CH3:31])[O:23][C:19]=3[CH:18]=2)=[CH:10][N:9]=1)[CH3:7])C.[OH-].[Na+]>CO>[C:26]1([CH3:31])[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[NH:24][C:22]1[O:23][C:19]2[CH:18]=[C:17]([CH2:16][C:15]([NH:14][C:11]3[CH:12]=[CH:13][C:8]([CH:6]([CH3:7])[CH2:5][C:4]([OH:35])=[O:3])=[N:9][CH:10]=3)=[O:34])[CH:33]=[CH:32][C:20]=2[N:21]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 9890975(3RS)-3-{5-[2-(2-o-tolylamino-benzoxazol-6-yl)-acetylamino]-pyrid-2-yl}-butyric acid ethyl ester

Produkt 1

HCID 9955119(3RS)-3-{5-[2-(2-o-Tolylamino-benzoxazol-6-yl)-acetylamino]-pyrid-2-yl}-butyric acidAusbeute 21,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of (3RS)-3-{5-[2-(2-o-tolylamino-benzoxazol-6-yl)-acetylamino]-pyrid-2-yl}-butyric acid ethyl ester (0.3 g, Reference Example 1) in methanol (4 mL) was treated with aqueous sodium hydroxide solution (1.5 mL, 1M) and left to stand in a water bath at 40° C. for three hours. The mixture was partially evaporated, diluted with more water and partially evaporated again. The residue was diluted with water (10 mL) and washed with diethyl ether (10 mL). The pH of the aqueous phase was adjusted to 7 by addition of dilute hydrochloric acid. The resulting white solid was filtered then dried and then triturated with boiling acetonitrile to give the title compound (0.06 g) as a white powder, m.p. 195-196° C. (with decomposition). MS: 445 (MH+).

Aufarbeitung

  1. waitleft
  2. customThe mixture was partially evaporated
  3. additiondiluted with more water
  4. custompartially evaporated again
  5. additionThe residue was diluted with water (10 mL)
  6. washwashed with diethyl ether (10 mL)
  7. additionThe pH of the aqueous phase was adjusted to 7 by addition of dilute hydrochloric acid
  8. filtrationThe resulting white solid was filtered
  9. customthen dried
  10. customtriturated with boiling acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-c1fd46ca1a8e474b914c39dd8cb81e45
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706738B2

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