تفاعل #7278

معادلة التفاعل

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

المردود 116.9%

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

المردود 116.9%

المذيبات

CH2Cl2

sodium bicarbonate

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   أخرىthe aqueous layer was separated
2. 2
   استخلاصextracted with CH2Cl2 (2×15 mL)
3. 3
   تجفيفThe combined organic phases were dried (Na2SO4)
4. 4
   ترشيحfiltered
5. 5
   أخرىevaporated in vacuo
6. 6
   أخرىto give the crude product as a white foam
7. 7
   أخرىPurification by column chromatography on silica gel (CH2Cl2/MeOH, 96:4)

الإجراء التجريبي

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.

المصدر