Nicotinic Acid → [((alpha-Nicotinoyloxyisobutoxy)carbonyl]aminomethyl}-1-Cyclohexane Acetic Acid

HRID 554040Notes

Reaction equation

HRID 554040 reaction equation
Cl[CH:2]([O:6][C:7]([NH:9][CH2:10][C:11]1([CH2:17][C:18]([OH:20])=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:8])[CH:3]([CH3:5])[CH3:4].N12CCCN=C1CCCCC2.[C:32]([OH:40])(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[N:35][CH:34]=1>CC(C)=O>[C:32]([O:40][CH:2]([O:6][C:7]([NH:9][CH2:10][C:11]1([CH2:17][C:18]([OH:20])=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:8])[CH:3]([CH3:5])[CH3:4])(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[N:35][CH:34]=1

Participants

5

Reactant 3

HCID 938Nicotinic AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 226420071-{[(alpha-Chloroisobutoxy)carbonyl]aminomethyl}-Cyclohexane Acetic Acid

Product 1

HCID 11959211[((alpha-Nicotinoyloxyisobutoxy)carbonyl]aminomethyl}-1-Cyclohexane Acetic AcidYield 14.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of (93) (268 mg, 0.88 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (158 μL, 1.01 mmol), and nicotinic acid (637 mg, 5.2 mmol) in acetone was stirred at room temperature for 48 h. After filtration, the filtrate was concentrated in vacuo and the resulting residue was purified by reverse phase preparative HPLC to afford 50 mg (14%) of the title compound. 1H NMR (CD3OD, 400 MHz): δ 1.07 (d, J=6.8 Hz, 3H), 1.09 (d, J=6.8 Hz, 3H), 1.32-1.58 (m, 10H), 2.19 (m, 1H), 2.26 (s, 2H), 3.23 (m, 2H), 6.78 (d, J=4.8 Hz, 1H), 7.58 (m, 1H), 8.39 (d, J=6.4 Hz, 1H), 8.76 (d, J=4.4 Hz, 1H), 9.10 (s, 1H). MS (ESI) m/z 393.42 (M+H+).

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customthe resulting residue was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-24cde608c34e414db6302ebb6e64cf52
Source dataset
uspto-grants-2011_11
Patent number
US08048917B2

Reaction notes

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