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

HRID 2230435ノート

反応式

HRID 2230435 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-036a4bd431704092b580f83d59bd14a9
出典データセット
uspto-grants-2002_07
特許番号
US06423840B1

反応ノート

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