Trifluoroacetic acid → Benzyl-2-[2-(tert-butoxycarbonyl)-acetamido]acetate

HRID 1616998ノート

反応式

HRID 1616998 の反応式
[CH2:1]([O:8][C:9](=[O:12])[CH2:10][NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:13](O)([C:15](F)(F)F)=[O:14].[C:20]([O:24][C:25](=[O:31])NCC(=O)N)([CH3:23])([CH3:22])[CH3:21].CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C>ClCCl>[CH2:1]([O:8][C:9](=[O:12])[CH2:10][NH:11][C:13](=[O:14])[CH2:15][C:25]([O:24][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 5

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 409140Benzyl glycinateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 109100641,1-Dimethylethyl N-(2-amino-2-oxoethyl)carbamate

生成物 1

HCID 68088972Benzyl-2-[2-(tert-butoxycarbonyl)-acetamido]acetate収率 72.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Benzyl-2-aminoacetate, TFA salt (13; 1.72 g, 5.12 mmol) and carbamoylmethyl-carbamic acid tert-butyl ester (8a; 1.13 g, 6.19 mmol) were dissolved in 40 mL dichloromethane with stirring at 0° C., followed by addition of N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (EDC; 1.33 g, 7.0 mmol) and triethylamine (1.0 mL, 7.2 mmol), and the reaction was replaced under room temperature with continuous stirring for 6 h. After the reaction was completed, dichloromethane was removed by concentration under reduced pressure. The obtained solid was dissolved in ethyl acetate (50 mL), and then the organic phase was washed by H2O, 5% citric acid, H2O, saturated NaHCO3 and saturated NaCl solution separately, and dried over MgSO4 and concentrated under reduced pressure to remove ethyl acetate to obtain colorless oil-like 14 (1.15 g; 72.6%). 1H-NMR (200 MHz) (CDCl3) δ: 7.28-7.33 (m, 5H, ArH), 6.89 (br, s, 1H, CONHCH2), 5.36 (br, s, 1H, NHBOC), 5.13 (s, 2H, CO2CH2Ph), 4.04 (d, 2H, CH2CO2CH2Ph), 3.81 (d, 2H, CH2NHBOC), 1.40 [s, 9H, CO2C(CH3)3].

後処理

  1. customwas replaced under room temperature
  2. stirringwith continuous stirring for 6 h
  3. customdichloromethane was removed by concentration under reduced pressure
  4. dissolutionThe obtained solid was dissolved in ethyl acetate (50 mL)
  5. washthe organic phase was washed by H2O, 5% citric acid, H2O, saturated NaHCO3 and saturated NaCl solution separately
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customto remove ethyl acetate

出典と根拠

ORDレコード
ord-d8b039c8ed704d629c795cd32c898d27
出典データセット
uspto-grants-2014_07
特許番号
US08765934B2

反応ノート

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