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

HRID 75706ノート

反応式

HRID 75706 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-0811e5819ad94353bf649156dfb9333c
出典データセット
uspto-grants-2014_09
特許番号
US08835458B2

反応ノート

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