تفاعل #2275706

ord-112f007386b94d00aeec85f29d85d94b

معادلة التفاعل

COC(=O)C(C)(C)NC(=O)c1ncc(OCc2ccccc2)cc1OCc1ccccc1
2-[(3,5-bis-benzyloxy-pyridine-2-carbonyl)-amino]-2-methylpropionic acid methyl ester
COC(=O)C(C)(C)NC(=O)c1ncc(O)cc1O
desired compound
المردود 94.0%
COC(=O)C(C)(C)NC(=O)c1ncc(O)cc1O
2-[(3,5-dihydroxy-pyridine-2-carbonyl)-amino]-2-methyl-propionic acid methyl ester
المردود 94.0%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    ترشيحThe reaction solution is filtered through Celite™
  2. 2
    غسيلthe collected solids are washed with hot MeOH
  3. 3
    تركيزThe combined filtrate and washings are concentrated under reduced pressure

الإجراء التجريبي

A solution of 2-[(3,5-bis-benzyloxy-pyridine-2-carbonyl)-amino]-2-methylpropionic acid methyl ester, 17, (0.58 g, 1.34 mmol) in MeOH (100 mL) containing 10% Pd/C (0.116 g) is stirred under an atmosphere of H2 for 22 hours. The reaction solution is filtered through Celite™ and the collected solids are washed with hot MeOH. The combined filtrate and washings are concentrated under reduced pressure to afford 0.321 g (94% yield) of the desired compound as a grey solid. 1H NMR (250 MHz, MeOD) δ ppm 7.67 (1H, d, J=2.4 Hz), 6.58 (1H, d, J=2.4 Hz), 3.69 (3H, s), 1.56 (6H, s). HPLC-MS: m/z 255 [M+H]+.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08323671B2uspto-grants-2012_12