4-Methoxyphenylacetic Acid → HCID 22146718, compound

HRID 1823831Notes

Reaction equation

HRID 1823831 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=O)=[CH:5][CH:4]=1.[CH2:13]([N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])[CH3:14].Cl.CN(C)CCCN=[C:27]=[N:28][CH2:29]C>ClCCl>[CH2:13]([N:15]1[CH2:18][CH2:19][CH:29]([N:28]([CH3:27])[C:10](=[O:12])[CH2:9][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[CH2:17][CH2:16]1)[C:14]1[CH:7]=[CH:8][CH:3]=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 76904-Methoxyphenylacetic AcidHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 22146718HCID 22146718, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Methoxyphenylacetic acid (895 mg, 5.39 mmol), triethylamine (2.40 ml, 17.1 mmol) and 1-(3-dimethylaminopropy)-3-ethyl-carbodiimide hydrochloride (1.12 g, 5.88 mmol) were added to a solution of the title compound of preparation 7 (1.00 g, 4.90 mmol) in dichloromethane (20 ml). The mixture was stirred for 12 hours at room temperature, then partitioned between dichloromethane and water. The aqueous layer was separated and extracted with dichloromethane (2×). The combined organic extracts were washed with brine, dried (MgSO4), filtered and evaporated under reduced pressure. The residual yellow oil was purified by column chromatography on silica gel using ethyl acetate:methanol (90:10) as eluant to afford the title compound as a clear oil, 1.26 g.

Sources & evidence

ORD record
ord-9ac656544663432286d9687649720baa
Source dataset
uspto-grants-2006_05
Patent number
US07041667B1

Reaction notes

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