Benzoic acid, 3-amino-, methyl ester → 3-[2-(4-Adamant-1-yl-phenoxy)-acetylamino]-benzoic acid methyl ester

HRID 1945369Notes

Reaction equation

HRID 1945369 reaction equation
[C:1]12([C:11]3[CH:21]=[CH:20][C:14]([O:15][CH2:16][C:17](O)=[O:18])=[CH:13][CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH3:22][O:23][C:24](=[O:32])[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([NH2:31])[CH:26]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH3:22][O:23][C:24](=[O:32])[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([NH:31][C:17](=[O:18])[CH2:16][O:15][C:14]2[CH:13]=[CH:12][C:11]([C:1]34[CH2:10][CH:5]5[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]5)[CH2:8]3)[CH2:2]4)=[CH:21][CH:20]=2)[CH:26]=1

Participants

7

Reactant 5

HCID 78274Benzoic acid, 3-amino-, methyl esterHCID 81531DiisopropylethylamineHCID 625381PMID26882240-Compound-8HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 39066833-[2-(4-Adamant-1-yl-phenoxy)-acetylamino]-benzoic acid methyl esterYield 76.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the (4-adamantan-1-yl-phenoxy)-acetic acid (140 mg, 0.5 mmol) and 3-aminobenzoic acid methyl ester (110 mg, 0.75 mmol) in DMF (5.0 mL) were added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDC) (144.0 mg, 0.75 mmol), 1-hydroxybenzotriazole hydrate (HOBT) (101 mg, 0.75 mmol), and N,N-diisopropylethylamine (DIPEA) (0.13 mL, 0.75 mmol). The reaction mixture was stirred at room temperature overnight, and then partitioned between ethyl acetate and brine. The organic phase was dried (MgSO4 anh), and concentrated. Purification by silica gel column chromatography (n-Hexane:Ethyl acetate:MeOH=15:3:1) gave 3-[2-(4-Adamant-1-yl-phenoxy)-acetylamino]-benzoic acid methyl ester as a white solid (160 mg, 76% yield).

Workup

  1. custompartitioned between ethyl acetate and brine
  2. dry with materialThe organic phase was dried (MgSO4 anh)
  3. concentrationconcentrated
  4. customPurification by silica gel column chromatography (n-Hexane:Ethyl acetate:MeOH=15:3:1)

Sources & evidence

ORD record
ord-8da9630b467b4fa4a395887f9342ce76
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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