Hydrochloric Acid → 5-(3-(7-Chloroquinolin-2-ylmethoxy)phenyl)-8-cyano-4,6-dithiaoctanoic acid

HRID 232419

반응식

HRID 232419 반응식
[C:1]([CH2:4][CH2:5][S:6][CH:7]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][C:22]2[CH:31]=[CH:30][C:29]3[C:24](=[CH:25][C:26]([Cl:32])=[CH:27][CH:28]=3)[N:23]=2)[CH:15]=1)[S:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])(=O)[NH2:2].N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.Cl>C1COCC1>[Cl:32][C:26]1[CH:25]=[C:24]2[C:29]([CH:30]=[CH:31][C:22]([CH2:21][O:20][C:16]3[CH:15]=[C:14]([CH:7]([S:6][CH2:5][CH2:4][C:1]#[N:2])[S:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])[CH:19]=[CH:18][CH:17]=3)=[N:23]2)=[CH:28][CH:27]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 199305168-Carbamyl-5-(3-(7-chloroquinolin-2-ylmethoxy)phenyl)-4,6-dithiaoctanoic acid

생성물 1

HCID 199305305-(3-(7-Chloroquinolin-2-ylmethoxy)phenyl)-8-cyano-4,6-dithiaoctanoic acid수율 84.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To the amide acid (Example 17) (2.788 g, 3.63 mmoles) in THF (40 mL) at -23° C., pyridine (2.2 mL, 7.5 equiv.) and trifluoroacetic anhydride (1.1 mL, 2.2 equiv.) were added. After one hour of stirring at 0° C., 10% HCl was added, the mixture was extracted with EtOAc, dried over sodium sulfate and evaporated. Flash chromatography on silica with EtOAc:toluene:AcOH 30:70:1 afforded 1.447 g of the title compound.

후처리

  1. extractionthe mixture was extracted with EtOAc
  2. dry with materialdried over sodium sulfate
  3. customevaporated

출처 및 근거

ORD 기록
ord-b418a5ee3af4401db1eaf82e8a648b37
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04851409

연결된 노트

불러오는 중…