N-(tert-butoxycarbonyl)glycine → {2-[4-(4-Fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethyl}-carbamic Acid tert-butyl Ester

HRID 11685ノート

反応式

HRID 11685 の反応式
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.CN(C)CCCN=C=NCC.[F:25][C:26]1[CH:40]=[CH:39][C:29]([CH2:30][N:31]2[CH2:36][C@H:35]([CH3:37])[NH:34][CH2:33][C@H:32]2[CH3:38])=[CH:28][CH:27]=1>ClCCl.CN(C)C1C=CN=CC=1>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]([N:34]1[CH2:33][C@H:32]([CH3:38])[N:31]([CH2:30][C:29]2[CH:39]=[CH:40][C:26]([F:25])=[CH:27][CH:28]=2)[CH2:36][C@H:35]1[CH3:37])=[O:12])([CH3:2])([CH3:3])[CH3:4]

参加物

6

反応物 3

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23405839(2R,5S)-1-(4-fluorobenzyl)-2,5-dimethylpiperazine

生成物 1

HCID 69655545{2-[4-(4-Fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethyl}-carbamic Acid tert-butyl Ester収率 94.3%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of tert-butoxycarbonylamino-acetic acid (0.71 g, 4.05 mmol) in dichloromethane (40 mL) was added 4-dimethylaminopyridine (0.74 g, 6.07 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.16 g, 6.07 mmol) and 1-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazine (0.90 g, 4.05 mmol). The reaction was stirred overnight at ambient temperature. The reaction was diluted with dichloromethane and washed with brine. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel gave the title compound (1.45 g).

後処理

  1. washwashed with brine
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f7f1d605a00c407485160438a0416ec8
出典データセット
uspto-grants-2006_08
特許番号
US07098212B2

反応ノート

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