Hydrochloric Acid → HCID 86748282, compound

HRID 264059

Reaction equation

HRID 264059 reaction equation
[C:1]([CH:3]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:4][C:5]([OH:7])=O)#[N:2].C(N(CC)CC)C.[CH3:21][O:22][C:23]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[C:26]([O:32][CH3:33])[C:24]=1[NH2:25].Cl.C1CCC(N=C=NC2CCCCC2)CC1>ClCCl>[C:1]([CH:3]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:4][C:5]([NH:25][C:24]1[C:26]([O:32][CH3:33])=[CH:27][C:28]([O:30][CH3:31])=[CH:29][C:23]=1[O:22][CH3:21])=[O:7])#[N:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 842712,4,6-TrimethoxyanilineHCID 111946253-Cyano-3-phenylpropanoic acid

Product 1

HCID 86748282HCID 86748282, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane (150 mL) solution of 3-cyano-3-phenylpropionic acid (5 g, 0.0286 mol) at 0° C. under a nitrogen atmosphere was added triethylamine (4 mL, 0.0286 mol) and 2,4,6-trimethoxyaniline.HCl (6.3 g, 0.0286 mol). To this solution was added DCC (6.2 g, 0.29 mol). The resulting mixture was allowed to warm to room temperature over 3 hours. This was then filtered and the filtrate partitioned between 1N HCl and dichloromethane. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The resulting solid (5.1 g) was recrystallized from dichloromethane/hexanes, mpt 157°-160° C.

Workup

  1. filtrationThis was then filtered
  2. customthe filtrate partitioned between 1N HCl and dichloromethane
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting solid (5.1 g) was recrystallized from dichloromethane/hexanes, mpt 157°-160° C.

Sources & evidence

ORD record
ord-d32b4e3cf5d2438cb998495b505814f9
Source dataset
uspto-grants-1997_07
Patent number
US05646170

Linked notes

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