تفاعل #1791

ord-c883c9ea34ed4863b03fce02c544723e

معادلة التفاعل

COC(=O)c1ccc(OC(=O)[C@H]2CC[C@@H](NC(=O)OC(C)(C)C)CC2)cc1OC
methyl 4-[N-Boc-cis-1-amino-4-cyclohexanoyloxy]-2-methoxybenzoate
O
H2O
O.[Li][OH]
LiOH.H2O
COc1cc(OC(=O)[C@H]2CC[C@@H](NC(=O)OC(C)(C)C)CC2)ccc1C(=O)O
4-[N-Boc-cis-1-amino-4-cyclohexanoyloxy]-2-methoxybenzoic acid

المذيبات

ظروف التفاعل

درجة الحرارة
45°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةcooled to ambient temperature
  2. 2
    أخرىThe solvent was removed under reduced pressure
  3. 3
    غسيلCH2Cl2 and eluted with same
  4. 4
    أخرىThe solvent was removed under reduced pressure

الإجراء التجريبي

To a stirred solution of methyl 4-[N-Boc-cis-1-amino-4-cyclohexanoyloxy]-2-methoxybenzoate (220 mg, 0.52 mmol) in THF:H2O (5 mL: 1 mL) was added LiOH.H2O (67.6 mg, 1.59 mmol). The reaction was heated to 45° C. over 12 h and then cooled to ambient temperature. The solvent was removed under reduced pressure. The crude solid passed through a plug of silca gel packed in 50:50 MeOH:CH2Cl2 and eluted with same. The solvent was removed under reduced pressure to afford 4-[N-Boc-cis-1-amino-4-cyclohexanoyloxy]-2-methoxybenzoic acid as a white solid.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05726172uspto-grants-1998_03