Diisopropylethylamine → (S)-tert-Butyl 4-(1-amino-3-(4'-cyanobiphenyl-4-yl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

HRID 216911ノート

反応式

HRID 216911 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]1([C:15]([OH:17])=O)[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:18][C@@H:19]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][CH:31]=2)=[CH:26][CH:25]=1)[C:20]([NH2:22])=[O:21].C(N(C(C)C)C(C)C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[NH2:22][C:20](=[O:21])[C@@H:19]([NH:18][C:15]([C:9]1([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1)=[O:17])[CH2:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]2[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][CH:31]=2)=[CH:28][CH:29]=1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 12682194-(Boc-amino)tetrahydropyran-4-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 59568596(S)-2-Amino-3-(4'-cyanobiphenyl-4-yl)propanamide

生成物 1

HCID 59568597(S)-tert-Butyl 4-(1-amino-3-(4'-cyanobiphenyl-4-yl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

4-(tert-Butoxycarbonylamino)tetrahydro-2H-pyran-4-carboxylic acid (374 mg), (S)-2-amino-3-(4′-cyanobiphenyl-4-yl)propanamide (Example 3, step (iii), 405 mg) and N-ethyl-N-isopropylpropan-2-amine (0.664 mL) were dissolved in DMF (10 mL) and to the solution was added TBTU (734 mg). The reaction mixture was stirred at room temperature for 2 days. The reaction mixture was evaporated to dryness, dissolved in dichloromethane (20 mL) and was absorbed onto silica. The product was purified by chromatography on silica eluting with 20% ethyl acetate in isohexane, then 50% ethyl acetate in isohexane and then 100% ethyl acetate to afford after evaporation of the relevant fractions the sub-titled compound (700 mg).

後処理

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutiondissolved in dichloromethane (20 mL)
  3. customwas absorbed onto silica
  4. customThe product was purified by chromatography on silica eluting with 20% ethyl acetate in isohexane
  5. custom50% ethyl acetate in isohexane and then 100% ethyl acetate to afford
  6. customafter evaporation of the relevant fractions the sub-titled compound (700 mg)

出典と根拠

ORDレコード
ord-9a565900734f40298ca770bec58354e8
出典データセット
uspto-grants-2012_06
特許番号
US08193239B2

反応ノート

読み込み中…