1-Naphthalenemethanamine → HCID 86587437, compound

HRID 1357842Notes

Reaction equation

HRID 1357842 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)C(O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:18]1([CH2:28][NH2:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1.C(P(=O)(OCC)[O:33][CH2:34]C)#N.C(N(CC)CC)C>C(#N)C>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([N:29]([CH2:28][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=2)[CH:34]=[O:33])[CH:15]=[CH:16][CH:17]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 83551-NaphthalenemethanamineHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 8541623-(((Tert-butoxy)carbonyl)amino)benzoic acid

Product 1

HCID 86587437HCID 86587437, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3-[(tert-butoxy)carbonylamino]benzoic acid (250 mg, 1.05 mmol), 1-naphthylmethylamine (170 mg, 1.05 mmol), diethyl cyanophosphonate (260 mg, 1.6 mmol), and triethylamine (0.22 ml, 1.6 mmol) in acetonitrile was stirred overnight. The solvent was evaporated, and the residue was partitioned between ethyl acetate and 1N HCl. The layers were separated, and the organic phase was washed twice more with 1N HCl, then 3 times each with water and brine. The solvent was removed in vacuo, and the crude product was purified on a silica gel column, eluting with 20% ethyl acetate in hexane, to deliver 270 mg of the amide.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between ethyl acetate and 1N HCl
  3. customThe layers were separated
  4. washthe organic phase was washed twice more with 1N HCl
  5. customThe solvent was removed in vacuo
  6. customthe crude product was purified on a silica gel column
  7. washeluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-04fa26de305b4bc8b9e431a75cb03048
Source dataset
uspto-grants-2003_07
Patent number
US06593362B2

Reaction notes

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