تفاعل #2275715

ord-427d8ca9ad2f4817b5a404659a2e8806

معادلة التفاعل

CC(C)(C)OC(=O)CNC(=O)c1ncc(O)cc1O
[(3,5-dihydroxy-pyridine-2-carbonyl)-amino]-acetic acid tert-butyl ester
O=C(O)C(F)(F)F
trifluoroacetic acid
O=C(O)CNC(=O)c1ncc(O)cc1O
desired compound
المردود 89.0%
O=C(O)CNC(=O)c1ncc(O)cc1O
[(3,5-dihydroxy-pyridine-2-carbonyl)-amino]-acetic acid
المردود 89.0%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    تركيزconcentrated under reduced pressure
  2. 2
    ترشيحThe solid that remains is collected by filtration
  3. 3
    غسيلwashed with Et2O

الإجراء التجريبي

To a solution of [(3,5-dihydroxy-pyridine-2-carbonyl)-amino]-acetic acid tert-butyl ester, 28, (0.10 g, 0.37 mmol) in CH2Cl2 (4 mL) at room temperature is added trifluoroacetic acid (1 mL). The reaction is stirred for 16 hours at room temperature and then concentrated under reduced pressure. The solid that remains is collected by filtration, washed with Et2O to afford 0.070 g (89% yield) of the desired compound as a colorless solid. 1H NMR (250 MHz, DMSO-d6) δ ppm 10.86 (1H, br s), 9.00 (1H, t, J=6.1 Hz), 7.77 (1H, d, J=2.4 Hz), 6.69 (1H, d, J=2.4 Hz), 3.95 (1H, d, J=6.2 Hz). HPLC-MS: m/z 213 [M+H]+.

المصدر

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