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HRID1012858

反应详情

EQUATION

反应方程式

HRID 1012858 的结构方程式

REACTANTS

反应物

6
结构：CCNCC
HCID8021

Diethylamine

C4H11N

结构：On1nnc2ccccc21
HCID75771

1-Hydroxybenzotriazole

C6H5N3O

结构：CCN(C(C)C)C(C)C
HCID81531

Diisopropylethylamine

C8H19N

结构：O=C(N[C@H](Cc1ccccc1)C(=O)O)OCC1c2ccccc2-c2ccccc21
HCID978332

未命名化合物

结构：CCN=C=NCCCN(C)C.Cl
HCID2723939

1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

C8H18ClN3

结构：COC(=O)CNC(=O)[C@H](NC(=O)[C@@H](CSC(c1ccccc1)(c1ccccc1)c1ccccc1)NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C
HCID57696983

未命名化合物

PRODUCTS

生成物

1
结构：COC(=O)CNC(=O)[C@H](NC(=O)[C@@H](CSC(c1ccccc1)(c1ccccc1)c1ccccc1)NC(=O)[C@@H](Cc1ccccc1)NC(=O)OCC1c2ccccc2-c2ccccc21)C(C)C
HCID87352571

未命名化合物

收率 80%

AUXILIARIES

试剂、催化剂与溶剂

3
结构：ClCCl
溶剂HCID6344

Dichloromethane

CH2Cl2

2 次

结构：CCCCCCC
溶剂HCID8900

Heptane

C7H16

结构：CC#N.ClCCl
溶剂HCID21877088

未命名化合物

PROCEDURE

实验过程

To a stirred solution of 3A (836 mg, 1.11 mmol) in CH3CN/CH2Cl2 (1:1, 60 mL) at RT was added Et2NH (3 mL). After stirring for 3 h at RT the reaction mixture was diluted with heptane (60 mL) and concentrated to give the crude amine as a colourless oil. To a stirred solution of Fmoc-D-phenylalanine (650 mg, 1.7 mmol) in CH2Cl2 (30 mL) was added EDAC.HCl (326 mg, 1.7 mmol), HOBt (230 mg, 1.7 mmol) and DIEA (627 μl, 3.6 mmol). After stirring at RT for 10 minutes a solution of the crude amine in CH2Cl2 (20 mL) was then added and the reaction mixture stirred for 12 h. Whereupon the reaction was washed with water (15 mL), 10% HCl (15 mL), 5% NaHCO3 (15 mL) and sat NaCl (15 mL) solutions, dried (Na2SO4), filtered, and the solvent removed to give an off white solid which was recrystallised from CH3CN to give 4B as a white solid (800 mg, 0.89 mmol, 80%): IR νmax 3264, 3053, 1742, 1701, 1636, 1532 cm−1; 1H-NMR (400 MHz, CDCl3) δ 7.75 (d, J=7.5 Hz, 2H), 7.46 (t, J=7.5 Hz, 2H), 7.41-7.31 (m, 8H), 7.30-7.07 (m, 16H), 7.01 (br s, 1H), 6.54 (br s, 2H), 5.29 (br s, 1H), 4.48-4.32 (m, 3H), 4.25-4.13 (m, 1H), 4.10 (t, J=8.5 Hz, 1H), 3.99-3.76 (m, 3H), 3.65 (s, 3H), 3.10-2.88 (m, 2H), 2.83-2.69 (m, 1H), 2.49 (dd, J=13.0, 6.3 Hz, 1H), 2.36-2.22, (m, 1H), 0.93 (t, J=7.0 Hz, 6H); 13C NMR 100 MHz 171.2 (C), 171.0 (C), 170.2 (C), 170.0 (C), 156.2 (C), 144.3 (C), 143.9 (C), 143.7 (C), 141.4 (C), 136.0 (C), 129.5 (CH), 129.3 (CH), 129.0 (CH), 128.3 (CH), 127.9 (CH), 127.4 (CH), 127.2 (CH), 127.1 (CH), 125.2 (CH), 120.1 (CH), 67.3 (CH2), 58.6 (CH), 56.2 (CH), 52.8 (CH), 52.3 (CH3), 47.2 (CH), 41.0 (CH2), 38.3 (CH2), 33.5 (CH2), 30.2 (CH), 19.4 (CH3), 17.7 (CH3); LRMS (ES+) m/z 1828 (30%, [2M+Na]+), 925 (100%, [M+Na]+).

WORKUP

后处理

  1. concentrationconcentrated
  2. customto give the crude amine as a colourless oil
  3. additionwas then added
  4. stirringthe reaction mixture stirred for 12 h
  5. washWhereupon the reaction was washed with water (15 mL), 10% HCl (15 mL), 5% NaHCO3 (15 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customthe solvent removed
  9. customto give an off white solid which
  10. customwas recrystallised from CH3CN