Triethylamine → N-[(R)-1-(6-bromo-3-fluoro-pyridin-2-yl)-2-((R)-1-cyano-2,2,2-trifluoro-1-methyl-ethoxy)-1-methyl-ethyl]-4-nitro-benzenesulfonamide

HRID 538369노트

반응식

HRID 538369 반응식
[Br:1][C:2]1[N:7]=[C:6]([C@:8]([NH:21][S:22]([C:25]2[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=2)(=[O:24])=[O:23])([CH3:20])[CH2:9][O:10][C@@:11]([CH3:19])([C:15]([F:18])([F:17])[F:16])[C:12]([NH2:14])=O)[C:5]([F:34])=[CH:4][CH:3]=1.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[N:7]=[C:6]([C@:8]([NH:21][S:22]([C:25]2[CH:26]=[CH:27][C:28]([N+:31]([O-:33])=[O:32])=[CH:29][CH:30]=2)(=[O:23])=[O:24])([CH3:20])[CH2:9][O:10][C@@:11]([C:12]#[N:14])([CH3:19])[C:15]([F:18])([F:17])[F:16])[C:5]([F:34])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 8471Triethylamine2회HCID 9845Trifluoroacetic anhydride2회HCID 86668077(R)-2-[(R)-2-(6-Bromo-3-fluoro-pyridin-2-yl)-2-(4-nitro-benzenesulfonylamino)-propoxy]-3,3,3-trifluoro-2-methyl-propionamide

생성물 1

HCID 86668078N-[(R)-1-(6-bromo-3-fluoro-pyridin-2-yl)-2-((R)-1-cyano-2,2,2-trifluoro-1-methyl-ethoxy)-1-methyl-ethyl]-4-nitro-benzenesulfonamide수율 99.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
2.5 °C

실험 절차

A suspension of (R)-2-[(R)-2-(6-bromo-3-fluoro-pyridin-2-yl)-2-(4-nitro-benzenesulfonylamino)-propoxy]-3,3,3-trifluoro-2-methyl-propionamide (8.43 g, 14.70 mmol) and triethylamine (5.12 ml, 36.8 mmol) in 85 ml DCM was cooled to 0-5° C. Trifluoroacetic anhydride (2.49 ml, 17.64 mmol) was added dropwise over 30 min. Additional triethylamine (1.54 ml, 11.07 mmol) and trifluoroacetic anhydride (0.75 ml, 5.29 mmol) were added to complete the reaction. The reaction mixture was quenched by addition of 14 ml aqueous ammonia (25%) and 14 ml water. The emulsion was stirred for 15 min, more water and DCM were added and the layers were separated. The organic layer was dried with MgSO4H2O, filtered and evaporated. Purification by column chromatography on a silica gel (hexanes/10-25% EtOAc) gave 8.09 g of the title compound as a yellow resin.

후처리

  1. customthe reaction
  2. customThe reaction mixture was quenched by addition of 14 ml aqueous ammonia (25%) and 14 ml water
  3. additionmore water and DCM were added
  4. customthe layers were separated
  5. dry with materialThe organic layer was dried with MgSO4H2O
  6. filtrationfiltered
  7. customevaporated
  8. customPurification by column chromatography on a silica gel (hexanes/10-25% EtOAc)

출처 및 근거

ORD 기록
ord-d985c6b6f50a49a0ba84fe870e56369c
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865712B2

반응 노트

불러오는 중…