Methanol → [4-(Benzyloxy)-3-methylquinolin-2-yl]methylpentylcarbamate

HRID 384444Notes

Reaction equation

HRID 384444 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([CH2:19][OH:20])[C:10]=1[CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22]([N:27]=[C:28]=[O:29])[CH2:23][CH2:24][CH2:25][CH3:26].CO>C1COCC1>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([CH2:19][O:20][C:28](=[O:29])[NH:27][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:10]=1[CH3:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 206036Pentane, 1-isocyanato-2×HCID 68508380[4-(Benzyloxy)-3-methylquinolin-2-yl]methanol

Product 1

HCID 59527290[4-(Benzyloxy)-3-methylquinolin-2-yl]methylpentylcarbamateYield 101.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [4-(benzyloxy)-3-methylquinolin-2-yl]methanol (105 mg) in THF (3 mL) was added pentylisocyanate (45 mg), followed by stirring at room temperature for 1 hour. Pentylisocyanate (20 mg) was further added to the reaction mixture, followed by stirring at room temperature for 16 hours. Methanol (2 mL) was added to the reaction mixture, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform) to obtain [4-(benzyloxy)-3-methylquinolin-2-yl]methylpentylcarbamate (150 mg).

Workup

  1. stirringby stirring at room temperature for 16 hours
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (eluent: chloroform)

Sources & evidence

ORD record
ord-0db15d37f6cd4dbbbea5af4561d0a284
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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