Hydrochloric Acid → 6-[(Tert-butoxy)carbonyl]pyridine-3-carboxylic acid

HRID 350405

반응식

HRID 350405 반응식
[C:1]([O:5][C:6]([C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][N:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>C1COCC1.C[C@H]1O[C@H]2[C@H](O)[C@@H](O)[C@H](OC3C4C(=CC5OCOC=5C=4)[C@@H](C4C=C(OC)C(O)=C(OC)C=4)[C@@H]4[C@@H]3COC4=O)O[C@@H]2CO1.C1COP(NCCCl)(=O)N(CCCl)C1.[NH2-].[NH2-].Cl[Pt+2]Cl>[C:1]([O:5][C:6]([C:8]1[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[CH:10][N:9]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 543263102-Tert-butyl 5-methyl pyridine-2,5-dicarboxylate

생성물 1

HCID 222714476-[(Tert-butoxy)carbonyl]pyridine-3-carboxylic acid수율 76%

시약·촉매·용매 2

HCID 56841950ICE protocol 1촉매HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of methyl 6-tert-butoxycarbonylnicotinate (1.2 g, 5.06 mmol) in THF (15 ml) and 0.25 N NaOH (40 ml, 10 mol) at an ambient temperature for 0.5 hr. The mixture was poured into ice-1 N HCl (10 ml). The solid was collected, washed with water and air-dried. The crude solid was recrystallized from CHCl3-EtOH-IPE to afford 6-tert-butoxycarbonylnicotinic acid (850 mg, 76%) as needles. IR (KBr) n3095, 1728, 1705 cm−1; 1H-NMR (DMAO-d6) δ 1.63 (s, 9 H), 8.09 (m, 1 H), 8.17 (m, 1 H), 8.42 (dt, J=2.4 and 8.3 Hz, 1 H), 9.21 (t, J=2.4 and 8.8 Hz, 1 H); MS (FAB) m/z 224 (M++1); Anal. Calcd for C29H33N3O6: C, 36.18; H, 3.18; N, 3.84. Found: C, 36.85; H, 3.35; N, 3.79.

후처리

  1. customThe solid was collected
  2. washwashed with water
  3. customair-dried
  4. customThe crude solid was recrystallized from CHCl3-EtOH-IPE

출처 및 근거

ORD 기록
ord-7757f7804b764518a6dbfa2b2a7862d8
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179819B2

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