Allylamine → (S)-tert-butyl 1-(allylamino)-1-oxobutan-2-ylcarbamate

HRID 1039025ノート

反応式

HRID 1039025 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH3:14])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.O[N:17]1[C:21]2C=CC=[CH:25][C:20]=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.C(N)C=C>ClCCl>[CH2:21]([NH:17][C:10](=[O:12])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:13][CH3:14])[CH:20]=[CH2:25]

参加物

7

反応物 5

HCID 7853AllylamineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2755934(S)-2-((tert)-Butoxycarbonyl)amino)butanoic acidHCID 27960291-Hydroxybenzotriazole hydrate

生成物 1

HCID 86654756(S)-tert-butyl 1-(allylamino)-1-oxobutan-2-ylcarbamate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A 500 mL round bottom flask was charged with (S)-2-(tert-butoxycarbonylamino)butanoic acid (5.0 g, 0.025 mol), 1-hydroxybenzotriazole hydrate (3.4 g, 0.025 mol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (7.2 g, 0.038 mol), and dichloromethane (125 mL). Triethylamine (7.6 mL, 0.055 mol) and allylamine (1.9 g, 0.025 mol) were added and the resulting mixture stirred at room temperature for 22 h. The resulting mixture was then diluted with dichlormethane (300 mL), washed 1× with 1N HCl (200 mL), 1× with 1N NaOH (200 mL), and 1× with water (200 mL). The organic layer was dried with sodium sulfate, filtered, and concentrated in vacuo to yield (S)-tert-butyl 1-(allylamino)-1-oxobutan-2-ylcarbamate. 1H NMR (300 MHz, CDCl3) δ 5.77-5.88 (m, 1H), 5.15-5.23 (m, 2H), 4.03-4.19 (m, 1H), 3.88-3.92 (m, 2H), 1.82-1.94 (m, 1H), 1.60-1.72 (m, 1H), 1.45 (s, 9H), and 0.96 (t, J=7.4 Hz, 3H).

後処理

  1. washwashed 1× with 1N HCl (200 mL), 1× with 1N NaOH (200 mL), and 1× with water (200 mL)
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-eeae5466e5084f8381a266aa1c82a80e
出典データセット
uspto-grants-2013_10
特許番号
US08552032B2

反応ノート

読み込み中…