Ammonium Chloride → Methyl 2-(5-(4-aminophenyl)thiazole-2-carboxamido)-3-methylbutanoate

HRID 1024431

반응식

HRID 1024431 반응식
[Cl-].[NH4+].[CH3:3][CH:4]([CH3:27])[CH:5]([NH:10][C:11]([C:13]1[S:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=2)=[CH:16][N:17]=1)=[O:12])[C:6]([O:8][CH3:9])=[O:7]>CCO.C1COCC1.O.[Fe]>[NH2:24][C:21]1[CH:22]=[CH:23][C:18]([C:15]2[S:14][C:13]([C:11]([NH:10][CH:5]([CH:4]([CH3:27])[CH3:3])[C:6]([O:8][CH3:9])=[O:7])=[O:12])=[N:17][CH:16]=2)=[CH:19][CH:20]=1

참가 물질

7

반응물 2

HCID 25517Ammonium ChlorideHCID 67150324Methyl 3-methyl-2-(5-(4-nitrophenyl)thiazole-2-carboxamido)butanoate2회

생성물 1

HCID 67150329Methyl 2-(5-(4-aminophenyl)thiazole-2-carboxamido)-3-methylbutanoate수율 92.3%

시약·촉매·용매 4

HCID 23925Iron촉매HCID 702Ethanol용매HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

반응 조건

온도
80 °C

실험 절차

Ammonium chloride (1.04 g) and iron (777 mg) were added to a solution of Methyl 3-methyl-2-(5-(4-nitrophenyl)thiazole-2-carboxamido)butanoate (Intermediate 2, step C, 2.15 g) in EtOH (21.5 ml), THF (8.6 ml), and Water (8.6 ml). The reaction mixture was refluxed at 80° C. for 3 hours. It was then cooled, filtered through celite and the solvent was removed under reduced pressure to get dark brown residue. The residue was taken in water and extracted with ethyl acetate. The organic layer was separated, dried over Na2SO4 and concentrated to get dark brown residue which was purified by column on silica gel in 2.5:7.5 EtOAc:chloroform to get yellow sticky solid which was crystallized in DCM/pet ether to yield 1.82 g (91%) of the title compound. 1HNMR (DMSO-d6, 300 MHz): δ 8.59 (d, 1H), 8.15 (s, 1H), 7.42 (d, 2H), 6.63 (d, 2H), 5.76 (bs, 2H), 4.31 (m, 1H), 3.67 (s, 3H), 2.27 (m, 1H), 0.91 (d, 6H); MS (ES+): m/z 334 (M+1).

후처리

  1. temperatureIt was then cooled
  2. filtrationfiltered through celite
  3. customthe solvent was removed under reduced pressure
  4. customto get dark brown residue
  5. extractionextracted with ethyl acetate
  6. customThe organic layer was separated
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customto get dark brown residue which
  10. customwas purified by column on silica gel in 2.5:7.5 EtOAc
  11. customchloroform to get yellow sticky solid which
  12. customwas crystallized in DCM/pet ether

출처 및 근거

ORD 기록
ord-daf9ccc5ba91423eab22caed2f04b704
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722901B2

연결된 노트

불러오는 중…