Hydrazine hydrate (1:1) → (S)-tert-Butyl (1-hydrazinyl-1-oxo-3-phenylpropan-2-yl)carbamate

HRID 339273ノート

反応式

HRID 339273 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:10](OC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[NH2:22][NH2:23]>CO>[NH:22]([C:10](=[O:11])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[NH2:23]

参加物

4

反応物 2

HCID 24654Hydrazine hydrate (1:1)HCID 9882138Boc-L-phenylalanine methyl ester

生成物 1

HCID 6710869(S)-tert-Butyl (1-hydrazinyl-1-oxo-3-phenylpropan-2-yl)carbamate収率 65.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-phenylpropanoate (Aldrich, 300 mg, 1.07 mmol) in MeOH (5.4 mL) was added hydrazine hydrate (170 μL, 3.44 mmol). The resulting solution was stirred at room temperature overnight and then concentrated in vacuo. The residue was triturated with hexanes (2×) and then from a minimal amount of 2:3 hexanes/MeOH (2×) to give the title compound (195 mg, 65%) as a white solid. 1H NMR (CDCl3) δ 7.41-7.25 (m, 3H), 7.20 (d, J=6.8 Hz, 2H), 4.39-4.21 (m, 1H), 3.07 (d, J=7.0 Hz, 2H), 1.42 (s, 9H); MS (ESI+) m/z 280.3 (M+H)+.

後処理

  1. concentrationconcentrated in vacuo
  2. customThe residue was triturated with hexanes (2×)

出典と根拠

ORDレコード
ord-8deb19f9a01541dea5cbd3f514200779
出典データセット
uspto-grants-2014_11
特許番号
US08889712B2

反応ノート

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