Benzoic acid, 3-amino-, methyl ester → HCID 86760244, compound

HRID 2213539Notes

Reaction equation

HRID 2213539 reaction equation
[C:1]12([O:11][CH2:12][C:13](=[C:15]3[C:20](=[O:21])OC(C)(C)OC3=O)[OH:14])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH3:25][O:26][C:27](=[O:35])[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([NH2:34])[CH:29]=1>CN(C1C=CN=CC=1)C.C1C=CC=CC=1>[CH3:25][O:26][C:27](=[O:35])[C:28]1[CH:29]=[C:30]([NH:34][C:20](=[O:21])[CH2:15][C:13](=[O:14])[CH2:12][O:11][C:1]23[CH2:10][CH:5]4[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]4)[CH2:8]2)[CH2:2]3)[CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 2

HCID 78274Benzoic acid, 3-amino-, methyl esterHCID 54718313HCID 54718313, compound

Product 1

HCID 86760244HCID 86760244, compoundYield 68.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 241BenzeneSolvent

Procedure

A mixture of 5-[2-(adamantan-1-yloxy)-1-hydroxy-ethylidene]-2,2-dimethyl-[1,3]dioxane-4,6-dione (27.27 g, 81.1 mmol), 3-amino-benzoic acid methyl ester (11.68 g, 77.2 mmol) and DMAP (cat.) in benzene (550 mL) was heated at reflux for 2 hours. The mixture was allowed to cool to room temperature. The solvent was removed by evaporation at reduced to give the crude product as a red oil. Purification by flash column chromatography (DCM:ethyl acetate 6:1) yielded the title compound as a yellow foam (20.34 g, 68%). 1H NMR (CDCl3) 9.22 (1H, br s), 8.08-8.07 (1H, t), 7.91-7.88 (1H, m), 7.81-7.77 (1H, m), 7.43-7.38 (1H, m), 4.14 (2H, s), 3.91 (3H, s), 3.74 (2H, s), 2.19 (3H, br s), 1.83-1.58 (12H, m).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. customThe solvent was removed by evaporation
  4. customto give the crude product as a red oil
  5. customPurification by flash column chromatography (DCM:ethyl acetate 6:1)

Sources & evidence

ORD record
ord-f61ace85046641ebb19ba7c28dcc912a
Source dataset
uspto-grants-2006_09
Patent number
US07105558B2

Reaction notes

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