Methylamine → HCID 18973823, compound

HRID 2395030Notes

Reaction equation

HRID 2395030 reaction equation
[CH3:1][NH2:2].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](OCC2C=CC=CC=2)=[O:18])=[CH:13][C:12]=1[CH2:27][CH2:28][CH2:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([OH:36])=[O:35])=[CH:32][CH:31]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)C>[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:18])[NH:2][CH3:1])=[CH:13][C:12]=1[CH2:27][CH2:28][CH2:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([OH:36])=[O:35])=[CH:32][CH:31]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 18973759HCID 18973759, compound

Product 1

HCID 18973823HCID 18973823, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To a 33% solution (16 ml) of methylamine in ethanol was added 4-[3-(2-benzyloxy-5-benzyloxycarbonylphenyl)propyl]benzoic acid (1.25 g). The mixture was heated at 100° C. for 12 hours in an autoclave. The solvent was evaporated and the residue extracted with ethyl acetate (100 ml) and washed with 1N aqueous HCl (100 ml) , dried (MgSO4), filtered and evaporated. The residue was subjected to chromatography on silica gel, eluting with EtOAc. The title product was purified by trituration with diethyl ether (150 mg) mpt. 163°-166° C.

Workup

  1. customThe solvent was evaporated
  2. extractionthe residue extracted with ethyl acetate (100 ml)
  3. washwashed with 1N aqueous HCl (100 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. washeluting with EtOAc
  8. customThe title product was purified by trituration with diethyl ether (150 mg) mpt
  9. custom163°-166° C.

Sources & evidence

ORD record
ord-51976286f3d04adfa9af3687fa933b1d
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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