Diisopropylethylamine → (S)-tert-butyl 3-(benzyloxycarbonylamino)-2-oxo-1,4'-bipiperidine-1'-carboxylate

HRID 407926ノート

反応式

HRID 407926 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][CH2:17][CH2:18][NH:19][CH:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]1)[C:13](O)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(N=C=NCCCN(C)C)C.C(N(C(C)C)C(C)C)C>CN(C=O)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:16][CH2:17][CH2:18][N:19]([CH:20]2[CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:31])([CH3:32])[CH3:30])=[O:27])[CH2:24][CH2:25]2)[C:13]1=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58787298(S)-2-(benzyloxycarbonylamino)-5-(1-(tert-butoxycarbonyl)piperidin-4-ylamino)pentanoic acid

生成物 1

HCID 58787267(S)-tert-butyl 3-(benzyloxycarbonylamino)-2-oxo-1,4'-bipiperidine-1'-carboxylate収率 61%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

Crude (S)-2-(benzyloxycarbonylamino)-5-(1-(tert-butoxycarbonyl)piperidin-4-ylamino)pentanoic acid (84 g, 187 mmol) was dissolved in DMF (600 mL), and cooled to 0° C. N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (35.8 g, 187 mmol) and N-ethyl-N-isopropylpropan-2-amine (32.5 mL, 187 mmol) were added and the reaction stirred at ambient temperature overnight. The reaction was concentrated and dissolved in EtOAc (1000 mL), washed with 1N HCl, saturated aqueous NaHCO3 and brine, dried over Na2SO4, filtered and concentrated. The residue was purified over silica gel (50% EtOAc in hexanes) to afford (S)-tert-butyl 3-(benzyloxycarbonylamino)-2-oxo-1,4′-bipiperidine-1′-carboxylate (49 g, 114 mmol, 60.8% yield) as white solid.

後処理

  1. concentrationThe reaction was concentrated
  2. dissolutiondissolved in EtOAc (1000 mL)
  3. washwashed with 1N HCl, saturated aqueous NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified over silica gel (50% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-9c135f3c0e2a4a55ade167de8f0ee53e
出典データセット
uspto-grants-2014_06
特許番号
US08754226B2

反応ノート

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