Semicarbazide → t-Butyl N-Allyloxycarbonyl-4-amino-5-oxopentanoate semicarbazone

HRID 2230435노트

반응식

HRID 2230435 반응식
[CH2:1]([O:4][C:5]([NH:7][CH:8]([CH:18]=[O:19])[CH2:9][CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=O)=[O:6])[CH:2]=[CH2:3].C([O-])(=O)C.[Na+].[NH2:25][NH:26][C:27]([NH2:29])=[O:28]>CO>[CH2:1]([O:4][C:5]([NH:7][CH:8]([CH:18]=[O:19])[CH2:9][CH2:10][C:11](=[N:25][NH:26][C:27]([NH2:29])=[O:28])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:6])[CH:2]=[CH2:3]

참가 물질

5

반응물 3

HCID 5196SemicarbazideHCID 517045Sodium AcetateHCID 18465646t-Butyl N-Allyloxycarbonyl-4-amino-5-oxopentanoate

생성물 1

HCID 54326573t-Butyl N-Allyloxycarbonyl-4-amino-5-oxopentanoate semicarbazone수율 73%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 207a (2.39 g, 8.8 mmol), in MeOH (20 ml) was added sodium acetate (0.72 g, 8.8 mmol) and semicarbazide (0.98 g, 8.8 mmol) stirred overnight, concentrated and diluted with CH2Cl2 (100 ml), washed with water, dried and concentrated. Flash chromatography (2% MeOH in CH2Cl2) afforded 208a (2.10 g, 73%) as an oil: [α]D20 −21 (c 2.55°, CH2Cl2); 1H NMR (CDCl3) δ9.98 (1H, s), 7.27 (1H, d), 5.8 (1H, m), 5.5 (1H, d), 5.35-5.19 (2H, m), 4.58 (2H, m), 4.14 (1H, m), 2.37 (2H, t), 2.09 (1H, m), 2.0-1.75 (2H, m); Anal. Calcd for C14H24N4O5: C, 51.21; H, 7.37; N, 17.06. Found: C, 50.2; H, 7.3; N, 16.1.

후처리

  1. concentrationconcentrated
  2. additiondiluted with CH2Cl2 (100 ml)
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-036a4bd431704092b580f83d59bd14a9
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06423840B1

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