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Methyl N-(triethylammoniosulfonyl)carbamate → tert-butyl 4-[(4S)-4-(methoxycarbonyl)-4,5-dihydro-1,3-oxazol-2-yl]-1H-indole-1-carboxylate

HRID 2389371
ノート
印刷プレビュー

反応式

HRID 2389371 の反応式
[OH:1][CH2:2][C@H:3]([NH:8][C:9]([C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[CH:14][N:15]2[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=O)[C:4]([O:6][CH3:7])=[O:5].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1.CCOC(C)=O>[CH3:7][O:6][C:4]([C@@H:3]1[CH2:2][O:1][C:9]([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[CH:14][N:15]3[C:20]([O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[O:21])=[N:8]1)=[O:5]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 68536502tert-butyl 4-({[(1S)-1-(hydroxymethyl)-2-methoxy-2-oxoethyl]amino}carbonyl)-1H-indole-1-carboxylate

生成物 1

HCID 68535383tert-butyl 4-[(4S)-4-(methoxycarbonyl)-4,5-dihydro-1,3-oxazol-2-yl]-1H-indole-1-carboxylate収率 68%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒
HCID 8857
Ethyl Acetate
溶媒

反応条件

温度
70 °C

実験手順

To a solution of tert-butyl 4-({[(1S)-1-(hydroxymethyl)-2-methoxy-2-oxoethyl]amino}carbonyl)-1H-indole-1-carboxylate (2.09 g) in THF (21.0 mL) was added Burgess Reagent (1.44 g) at ambient temperature and the mixture was stirred at 70° C. for 45 minutes. The resulting mixture was diluted with EtOAc (60 mL) and washed successively with saturated NaHCO3 aqueous solution and brine. The organic layer was dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=2:1) to afford tert-butyl 4-[(4S)-4-(methoxycarbonyl)-4,5-dihydro-1,3-oxazol-2-yl]-1H-indole-1-carboxylate (1.35 g) as a colorless amorphous.

後処理

  1. washwashed successively with saturated NaHCO3 aqueous solution and brine
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography (n-hexane:EtOAc=2:1)

出典と根拠

ORDレコード
ord-541ba14ba56642a286980a8b836473dd
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08273745B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート