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

HRID 49697Notes

Reaction equation

HRID 49697 reaction equation
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

Participants

4

Reactant 2

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

Product 1

HCID 9955119(3RS)-3-{5-[2-(2-o-Tolylamino-benzoxazol-6-yl)-acetylamino]-pyrid-2-yl}-butyric acidYield 21.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-c1fd46ca1a8e474b914c39dd8cb81e45
Source dataset
uspto-grants-2004_03
Patent number
US06706738B2

Reaction notes

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