Diisopropylcarbodiimide → 2-[N-(benzyloxycarbonyl)-N-methylamino]-N-[2-(3-tert-butyl-4-hydroxyphenyl)-1-methylethyl]-3-methylbutanamide

HRID 1383736노트

반응식

HRID 1383736 반응식
[C:1]([C:5]1[CH:6]=[C:7]([CH2:12][CH:13]([NH2:15])[CH3:14])[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[C:16]([N:26]([CH3:34])[C@H:27]([C:31](O)=[O:32])[CH:28]([CH3:30])[CH3:29])([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].C1C=CC2N(O)N=NC=2C=1.CC(C)N=C=NC(C)C>CN(C=O)C.C(OCC)(=O)C>[CH2:19]([O:18][C:16]([N:26]([CH:27]([CH:28]([CH3:30])[CH3:29])[C:31]([NH:15][CH:13]([CH3:14])[CH2:12][C:7]1[CH:8]=[CH:9][C:10]([OH:11])=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=1)=[O:32])[CH3:34])=[O:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

7

반응물 4

HCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 7016371N-Methyl-N-[(phenylmethoxy)carbonyl]-L-valineHCID 211874322-(3-Tert-butyl-4-hydroxyphenyl)-1-methylethylamine

생성물 1

HCID 211874312-[N-(benzyloxycarbonyl)-N-methylamino]-N-[2-(3-tert-butyl-4-hydroxyphenyl)-1-methylethyl]-3-methylbutanamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 0.31 g (1.50 mmol) of 2-(3-tert-butyl-4-hydroxyphenyl)-1-methylethylamine, 0.40 g (1.50 mmol) of Z-N-Me-Val-OH and 0.30 g (2.25 mmol) of HOBT in DMF (5 ml), 0.35 ml (2.25 mmol) of DIC was added under cooling with ice. After being stirred at room temperature for 2 hours, 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=125:1) to give 2-[N-(benzyloxycarbonyl)-N-methylamino]-N-[2-(3-tert-butyl-4-hydroxyphenyl)-1-methylethyl]-3-methylbutanamide in the amount of 0.55 g (81%).

후처리

  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=125:1)

출처 및 근거

ORD 기록
ord-b8c06b385d1d4476a397907547536259
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06255285B1

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