Ethanamine, 2,2,2-trifluoro- → (S)-tert-Butyl 1-oxo-1-(2-(2,2,2-trifluoroethylcarbamoyl)-1H-pyrrol-1-ylamino)propan-2-ylcarbamate

HRID 525037

반응식

HRID 525037 반응식
[F:1][C:2]([F:6])([F:5])[CH2:3][NH2:4].[C:7]([O:11][C:12]([NH:14][C@@H:15]([CH3:28])[C:16]([NH:18][N:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[C:24](OC)=[O:25])=[O:17])=[O:13])([CH3:10])([CH3:9])[CH3:8].C[Al](C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.O>[O:17]=[C:16]([NH:18][N:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[C:24](=[O:25])[NH:4][CH2:3][C:2]([F:6])([F:5])[F:1])[C@@H:15]([NH:14][C:12](=[O:13])[O:11][C:7]([CH3:10])([CH3:9])[CH3:8])[CH3:28]

참가 물질

7

반응물 4

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 13355Disodium 2,3-dihydroxybutanedioateHCID 16682925TrimethylaluminumHCID 86722033(S)-methyl 1-(2-(tert-butoxycarbonylamino)propanamido)-1H-pyrrole-2-carboxylate

생성물 1

HCID 86722056(S)-tert-Butyl 1-oxo-1-(2-(2,2,2-trifluoroethylcarbamoyl)-1H-pyrrol-1-ylamino)propan-2-ylcarbamate

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매2회

반응 조건

온도
80 °C

실험 절차

2,2,2-Trifluoroethanamine (680 microl, 8.66 mmols) was added to a solution of (S)-methyl 1-(2-(tert-butoxycarbonylamino)propanamido)-1H-pyrrole-2-carboxylate (900 mg, 2.89 mmols) in toluene (36 ml). A 2M solution of trimethyl aluminium in toluene (7 ml, 14.00 mmols) was added and it was stirred at 80° C. overnight. Water (50 ml) and a 0.5M solution of sodium tartrate (25 ml) were added. It was extracted with ethylacetate. The combined organic layers were washed with water and brine. It was dried, filtered and concentrated in vacuum. The title compound was obtained (1.021 g, 93%).

후처리

  1. extractionIt was extracted with ethylacetate
  2. washThe combined organic layers were washed with water and brine
  3. customIt was dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum

출처 및 근거

ORD 기록
ord-d4d0282b25874c5bb4f22d150445dae7
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340547B2

연결된 노트

불러오는 중…