Hydrochloric Acid → 2-((9S)-7-(4-chlorophenyl)-4,5,13-trimethyl-3-thia-1,8,11,12-tetraazatricyclo(8.3.0.0,2,6)trideca-2(6),4,7,10,12-pentaen-9-yl)acetic acid

HRID 874469

반응식

HRID 874469 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2=[N:9][C@@H:10]([CH2:24][C:25]([O:27]C)=[O:26])[C:11]3[N:12]([C:20]([CH3:23])=[N:21][N:22]=3)[C:13]3[S:17][C:16]([CH3:18])=[C:15]([CH3:19])[C:14]2=3)=[CH:4][CH:3]=1.O.[OH-].[Li+].Cl>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2=[N:9][C@@H:10]([CH2:24][C:25]([OH:27])=[O:26])[C:11]3[N:12]([C:20]([CH3:23])=[N:21][N:22]=3)[C:13]3[S:17][C:16]([CH3:18])=[C:15]([CH3:19])[C:14]2=3)=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 59190723MS417

생성물 1

HCID 668281072-((9S)-7-(4-chlorophenyl)-4,5,13-trimethyl-3-thia-1,8,11,12-tetraazatricyclo(8.3.0.0,2,6)trideca-2(6),4,7,10,12-pentaen-9-yl)acetic acid수율 87%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Methyl 2-((6S,Z)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)acetate (see e.g., WO 2006129623)(100.95 mg, 0.243 mmol was suspended in 1 mL methanol to which was added a freshly prepared solution of lithium hydroxide monohydrate (0.973 mL, 0.5 M, 0.487 mmol) and shaken at ambient temperature for 3 hours. The methanol was evaporated and the pH adjusted with aqueous hydrochloric acid (1 M, 0.5 mL, 0.5 mmol) and extracted four times with ethyl acetate. The combined ethyl acetate layers were dried over magnesium sulfate and evaporated to afford 2-((6S,Z)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)acetic acid (85.3 mg, 87.0%); ESI-MS m/z=401.1 [(M+H)+] which was used directly in the next reaction.

후처리

  1. customThe methanol was evaporated
  2. extractionextracted four times with ethyl acetate
  3. dry with materialThe combined ethyl acetate layers were dried over magnesium sulfate
  4. customevaporated

출처 및 근거

ORD 기록
ord-0d2b30a940eb43fca802612b19c6cb7b
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08980879B2

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