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

反応式

HRID 525037 の反応式
[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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒2 回

反応条件

温度
80 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-d4d0282b25874c5bb4f22d150445dae7
出典データセット
uspto-grants-2016_05
特許番号
US09340547B2

関連ノート

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