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

HRID 49697노트

반응식

HRID 49697 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-c1fd46ca1a8e474b914c39dd8cb81e45
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706738B2

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