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

HRID 850889
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HRID 850889 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매2회
HCID 6344Dichloromethane용매

실험 절차

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].

후처리

  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

출처 및 근거

ORD 기록
ord-e0c10ece33f44c8e8fd3e8180845a902
출처 데이터셋
uspto-grants-2000_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06018020

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