Benzyl Alcohol → (S)-benzyl 2-(tert-butoxycarbonylamino)-3,3-dimethylbutanoic acid

HRID 75706노트

반응식

HRID 75706 반응식
[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([OH:9])=[O:8])[C:3]([CH3:6])([CH3:5])[CH3:4].CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.[CH2:37](O)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>ClCCl.CN(C1C=CN=CC=1)C>[CH2:37]([C@:2]([NH:1][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([C:3]([CH3:6])([CH3:5])[CH3:4])[C:7]([OH:9])=[O:8])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

참가 물질

7

반응물 4

HCID 244Benzyl AlcoholHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 2734668(S)-2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic acid

생성물 1

HCID 131731871(S)-benzyl 2-(tert-butoxycarbonylamino)-3,3-dimethylbutanoic acid수율 99%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

Boc-Tle-OH (4.8 g, 22.3 mmol) was dissolved in dichloromethane (50 mL), and EDCI (4.3 g, 44.6 mmol), DMAP (0.6 g, 4.46 mmol), DIPEA (16 mL, 89.2 mmol), and benzyl alcohol (5 mL, 44.6 mmol) were added dropwise. The mixture was stirred at room temperature for 12 hours. The mixture was washed several times with an aqueous solution of 5% citric acid. The organic layer was dried over sodium sulfate, and filtered and distilled under reduced pressure to obtain the title compound as yellow oil (6.7 g, 99%).

후처리

  1. washThe mixture was washed several times with an aqueous solution of 5% citric acid
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. distillationdistilled under reduced pressure

출처 및 근거

ORD 기록
ord-0811e5819ad94353bf649156dfb9333c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835458B2

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