Ammonium Hydroxide → (S)-2-(4-((R)-4-(4-fluorophenyl)-4,5-dihydrooxazol-2-yl)phenyl)morpholine

HRID 710258노트

반응식

HRID 710258 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:11][C:12](=[O:25])[C:13]2[CH:18]=[CH:17][C:16]([C@@H:19]3[O:24][CH2:23][CH2:22][NH:21][CH2:20]3)=[CH:15][CH:14]=2)[CH2:9]O)=[CH:4][CH:3]=1.C(N(S(F)(F)F)CC)C.[OH-].[NH4+].CCCCCCC.C(OC(=O)C)C>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[CH2:9][O:25][C:12]([C:13]3[CH:18]=[CH:17][C:16]([C@@H:19]4[O:24][CH2:23][CH2:22][NH:21][CH2:20]4)=[CH:15][CH:14]=3)=[N:11]2)=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 14923Ammonium HydroxideHCID 123472(Diethylamino)sulfur trifluorideHCID 21899848Ethylacetate heptaneHCID 89689472N-((R)-1-(4-Fluorophenyl)-2-hydroxyethyl)-4-((S)-morpholin-2-yl)benzamide

생성물 1

HCID 71656895(S)-2-(4-((R)-4-(4-fluorophenyl)-4,5-dihydrooxazol-2-yl)phenyl)morpholine수율 37.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

N—((R)-1-(4-Fluorophenyl)-2-hydroxyethyl)-4-((S)-morpholin-2-yl)benzamide (14.4 mg, 0.042 mmol) was dissolved in dichloromethane (0.4 ml) and diethylaminosulfur trifluoride (DAST) (6.74 mg, 0.042 mmol) was added. The reaction mixture was allowed to stir at room temperature for 5 hours. The reaction mixture was poured over crushed ice mixed with 25% ammonium hydroxide solution (10 ml) and the solution was extracted twice with dichloromethane (2×10 ml). The combined organic layer was dried over MgSO4 and evaporated to give a sticky solid. Addition of heptane/ethy lacetate 4:1 and some drops of dichloromethane gave a white solid which was isolated by filtration and dried in vacuo to afford the product as a white solid (5.1 mg, 37%): MS (ISP): 327.2 ([M+H]+).

후처리

  1. additionThe reaction mixture was poured
  2. customover crushed ice
  3. extractionthe solution was extracted twice with dichloromethane (2×10 ml)
  4. dry with materialThe combined organic layer was dried over MgSO4
  5. customevaporated
  6. customto give a sticky solid
  7. customwas isolated by filtration
  8. customdried in vacuo

출처 및 근거

ORD 기록
ord-548e8f226ab34186af8e38e2b2f2c9a4
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181230B2

반응 노트

불러오는 중…