Diisopropylethylamine → 4-[2-(4-Adamantan-1-yl-phenoxy)acetyl-amino]-isophthalic acid dimethyl ester

HRID 1945381Notes

Reaction equation

HRID 1945381 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:36])[C:25]1[CH:34]=[CH:33][C:32]([NH2:35])=[C:27]([C:28]([O:30][CH3:31])=[O:29])[CH:26]=1.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:22][O:23][C:24](=[O:36])[C:25]1[CH:34]=[CH:33][C:32]([NH:35][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)=[C:27]([C:28]([O:30][CH3:31])=[O:29])[CH:26]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 625381PMID26882240-Compound-8HCID 11095854Dimethyl 4-aminoisophthalate

Product 1

HCID 248111044-[2-(4-Adamantan-1-yl-phenoxy)acetyl-amino]-isophthalic acid dimethyl esterYield 76.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of (4-adamantan-1-yl-phenoxy)-acetic acid (229 mg, 0.8 mmol) and 4-aminoisophthalic acid dimethyl ester (301 mg, 1.4 mmol) were dissolved in DMF (5 mL), and EDCHCl (140 mg, 0.75 mmol), HOAt (163 mg, 1.2 mmol) and DIPEA (0.21 ml, 1.2 mmol) was added. The mixture was stirred overnight, and then partitioned between ethyl acetate and brine. The organic phase was dried (MgSO4 anh), and concentrated. The residue was purified by silica gel column chromatography (CH2Cl2:MeOH=50:1) to give 4-[2-(4-Adamantan-1-yl-phenoxy)acetyl-amino]-isophthalic acid dimethyl ester as a white solid (281 mg, 76.3% yield).

Workup

  1. custompartitioned between ethyl acetate and brine
  2. dry with materialThe organic phase was dried (MgSO4 anh)
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (CH2Cl2:MeOH=50:1)

Sources & evidence

ORD record
ord-b870562caeab4dfe9e5facf45c95b975
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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