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Benzyl Alcohol → N-(tert-butoxycarbonyl)-3-cyclopentyl-L-alanine benzyl ester

HRID 850889
ノート
印刷プレビュー

反応式

HRID 850889 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:16]([OH:18])=[O:17])[CH2:10][CH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:19](O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.ClCCl>[CH2:19]([O:17][C:16](=[O:18])[C@H:9]([CH2:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15]1)[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 244Benzyl AlcoholHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 40418614N-(tert-Butoxycarbonyl)-3-cyclopentyl-L-alanine

生成物 1

HCID 54072905N-(tert-butoxycarbonyl)-3-cyclopentyl-L-alanine benzyl ester収率 95.5%

試薬・触媒・溶媒 2

HCID 14284
4-(Dimethylamino)pyridine
触媒
2 回
HCID 6344Dichloromethane溶媒

実験手順

A mixture of 1.2 g (4.67 mmol) of N-(tert-butoxycarbonyl)-3-cyclopentyl-L-alanine, 540 mg (5 mmol) of benzyl alcohol, 675 mg (5 mmol) of 1-hydroxybenzotriazole, 1.152 g (6 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 0.031 g (0.25 mmol) of 4-dimethylaminopyridine was stirred in 20 ml of dichloromethane for 1 hour and then a further 610 mg (5 mmol) of 4-dimethylaminopyridine were added. After 4 hours the solution was extracted with 2M hydrochloric acid and saturated sodium bicarbonate solution, dried over anhydrous magnesium sulphate and evaporated. The oil obtained was chromatographed on silica gel using ethyl acetate/ petrol (1:6) for the elution to give 1.55 g of N-(tert-butoxycarbonyl)-3-cyclopentyl-L-alanine benzyl ester as a colourless oil; MS: m/e 348 [M+H].

後処理

  1. extractionAfter 4 hours the solution was extracted with 2M hydrochloric acid and saturated sodium bicarbonate solution
  2. dry with materialdried over anhydrous magnesium sulphate
  3. customevaporated
  4. customThe oil obtained
  5. customwas chromatographed on silica gel
  6. washfor the elution

出典と根拠

ORDレコード
ord-e0c10ece33f44c8e8fd3e8180845a902
出典データセット
uspto-grants-2000_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06018020

反応ノート

読み込み中…

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