반응 #7278

반응 방정식

N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

N-(tert-butoxycarbonyl)-L-proline

N,N-diisopropylethylamine

1-hydroxybenzotriazole hydrate

1-(3-dimethylaminopropyl)-3-ethyl carbodiimide HCl

→

amide

수율 116.9%

(S)-Pyrrolidine-2-carboxylic acid 4-{[(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide

수율 116.9%

용매

CH2Cl2

sodium bicarbonate

CH2Cl2

반응 조건

후처리

1. 1
   기타the aqueous layer was separated
2. 2
   추출extracted with CH2Cl2 (2×15 mL)
3. 3
   건조The combined organic phases were dried (Na2SO4)
4. 4
   여과filtered
5. 5
   기타evaporated in vacuo
6. 6
   기타to give the crude product as a white foam
7. 7
   기타Purification by column chromatography on silica gel (CH2Cl2/MeOH, 96:4)

실험 절차

To a stirred solution of N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (148 mg, 0.37 mmol) in dry CH2Cl2 (5 mL) was added N-(tert-butoxycarbonyl)-L-proline (88 mg, 0.41 mmol), N,N-diisopropylethylamine (0.13 mL, 0.75 mmol), 1-hydroxybenzotriazole hydrate (68 mg, 0.50 mmol) and 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide HCl (EDC) (99 mg, 0.52 mmol) and the mixture stirred at room temperature overnight. The reaction mixture was diluted with CH2Cl2 (25 mL) and saturated aqueous sodium bicarbonate (30 mL) and the aqueous layer was separated and extracted with CH2Cl2 (2×15 mL). The combined organic phases were dried (Na2SO4), filtered and evaporated in vacuo to give the crude product as a white foam. Purification by column chromatography on silica gel (CH2Cl2/MeOH, 96:4) gave the desired amide (214 mg, 85%) as a white foam.

출처