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Piperidine → 2-(2-Amino-4-methyl-pentanoylamino)-3-(4-benzyloxy-phenyl)-propionic acid tert-butyl ester

HRID 2230287
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HRID 2230287 반응식
[C:1]([O:5][C:6](=[O:46])[CH:7]([NH:23][C:24](=[O:45])[CH:25]([NH:30]CC1C2C=CC=CC=2C2C1=CC=CC=2)[CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].N1CCCCC1>O1CCCC1>[C:1]([O:5][C:6](=[O:46])[CH:7]([NH:23][C:24](=[O:45])[CH:25]([NH2:30])[CH2:26][CH:27]([CH3:28])[CH3:29])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)([CH3:2])([CH3:4])[CH3:3]
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참가 물질

4

반응물 2

HCID 8082PiperidineHCID 545401193-(4-Benzyloxy-phenyl)-2-{2-[(9H-fluoren-9-ylmethyl)-amino]-4-methyl-pentanoylamino}-propionic acid tert-butyl ester

생성물 1

HCID 540817292-(2-Amino-4-methyl-pentanoylamino)-3-(4-benzyloxy-phenyl)-propionic acid tert-butyl ester수율 77%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of the product from Example AH (3-(4-benzyloxy-phenyl)-2-{2-[(9H-fluoren-9-ylmethyl)-amino]-4-methyl-pentanoylamino}-propionic acid tert-butyl ester) (12.2 g, 20.0 mmol) in 500 mL of tetrahydrofuran was treated with piperidine (80 mL). The resulting solution was stirred at room temperature for 48 hours. The reaction mixture was concentrated and the residue purified by chromatography (silica gel, gradient elution EtOAc—15% EtOH/EtOAc). The resulting yellow solid was broken up in heptane to give the title compound as a white solid (6.77 g, 77%), mp=56-60° C.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue purified by chromatography (silica gel, gradient elution EtOAc—15% EtOH/EtOAc)

출처 및 근거

ORD 기록
ord-7e4162ee82ef41908b8e26073b972a8e
출처 데이터셋
uspto-grants-2002_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06423689B1

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