Dimethylformamide → n-[2-(3-Tert-butyl-4-hydroxyphenyl)-1-methylethyl]-2-[n-(n-boc-phenyl-alanyl)-n-methylamino]-3-methylbutanamide

HRID 1383738ノート

反応式

HRID 1383738 の反応式
[C:1]([C:5]1[CH:6]=[C:7]([CH2:12][CH:13]([NH:15][C:16](=[O:23])[CH:17]([NH:21][CH3:22])[CH:18]([CH3:20])[CH3:19])[CH3:14])[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].N([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C@H](C(O)=O)CC1C=CC=CC=1.[CH:43]1[CH:44]=[CH:45][C:46]2N(O)N=[N:49][C:47]=2[CH:48]=1.[CH3:53][CH:54]([CH3:61])N=C=NC(C)C.CN(C=[O:66])C>C(OCC)(=O)C>[C:1]([C:5]1[CH:6]=[C:7]([CH2:12][CH:13]([NH:15][C:16](=[O:23])[CH:17]([N:21]([C:53](=[O:66])[C@H:54]([CH3:61])[N:49]([C:47]2[CH:48]=[CH:43][CH:44]=[CH:45][CH:46]=2)[C:36]([O:38][C:39]([CH3:41])([CH3:40])[CH3:42])=[O:37])[CH3:22])[CH:18]([CH3:19])[CH3:20])[CH3:14])[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:3])([CH3:2])[CH3:4]

参加物

7

反応物 5

HCID 6228DimethylformamideHCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 21187418N-[2-(3-tert-butyl-4-hydroxyphenyl)-1-methylethyl]-3-methyl-2-(methylamino)butanamide

生成物 1

HCID 20668311n-[2-(3-Tert-butyl-4-hydroxyphenyl)-1-methylethyl]-2-[n-(n-boc-phenyl-alanyl)-n-methylamino]-3-methylbutanamide

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 0.36 g (1.12 mmol) of N-[2-(3-tert-butyl-4-hydroxyphenyl)-l-methylethyl]-3-methyl-2-(methylamino)butanamide, 0.75 g (2.81 mmol) of Boc-Phe-OH and 0.38 g (2.81 mmol) of HOBT in DMF (5 ml), 0.44 ml (2.81 mmol) of DIC was added under cooling with ice. After being stirred at room temperature for 2.5 days, the reaction mixture was diluted with ethyl acetate and washed successively with saturated aqueous NaHCO3, water and saturated brine. The organic layer was dried with anhydrous magnesium sulfate and concentrated under reduced pressure; the resulting residue was subjected to silica gel column chromatography (eluting solvent; chloroform:methanol=80:1) to give N-[2-(3-tert-butyl-4-hydroxyphenyl)-1-methylethyl]-2-[N-(N-Boc-phenyl-alanyl)-N-methylamino]-3-methylbutanamide in 333 mg (52%).

後処理

  1. temperatureunder cooling with ice
  2. washwashed successively with saturated aqueous NaHCO3, water and saturated brine
  3. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washthe resulting residue was subjected to silica gel column chromatography (eluting solvent; chloroform:methanol=80:1)

出典と根拠

ORDレコード
ord-581dc2a28990486196642175164477e1
出典データセット
uspto-grants-2001_07
特許番号
US06255285B1

反応ノート

読み込み中…