2-Methoxybenzoic acid → HCID 59167753, compound

HRID 1616639Notes

Reaction equation

HRID 1616639 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:11])[CH2:9]N.[C:13]([OH:23])(=O)[C:14]1[C:15]([O:20][CH3:21])=[CH:16][CH:17]=[CH:18][CH:19]=1.Cl.C[N:26](CCCN=C=NCC)C.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:12])[CH2:4][CH2:5][CH2:6][CH:7]([NH:26][C:13](=[O:23])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH3:21])[C:8](=[O:11])[CH3:9]

Participants

8

Reactant 5

HCID 113702-Methoxybenzoic acidHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 86034752HCID 86034752, compound

Product 1

HCID 59167753HCID 59167753, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Combine a mixture of 7-amino-6-oxo-heptanoic acid methyl ester and 5-amino-6-oxo-heptanoic acid methyl ester hydrochlorides (2.36 g, 11.3 mmol) with o-anisic acid (1.71 g, 11.3 mmol), 1-(dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.16 g, 11.3 mmol), 1-hydroxybenzotriazole hydrate (11.3 mmol), N,N-diisopropylethylamine (5.88 mL, 33.8 mmol) in DMF and stir for 24-48 hours. Dilute the mixture with water and extract with EtOAc. Wash the combined extracts with brine and dry over Na2SO4 before concentrating. Chromatograph the residue over silica gel (MeOH/CH2Cl2) to allow for isolation of a mixture of 7-(2-methoxy-benzoylamino)-6-oxo-heptanoic acid methyl ester and 5-(2-methoxy-benzoylamino)-6-oxo-heptanoic acid methyl ester (3.45 g, 99%). MS (ES): (M+1)+ 308.1 m/z.

Workup

  1. extractionextract with EtOAc
  2. washWash the combined extracts with brine
  3. dry with materialdry over Na2SO4
  4. concentrationbefore concentrating
  5. additionChromatograph the residue over silica gel (MeOH/CH2Cl2) to allow for isolation of a mixture of 7-(2-methoxy-benzoylamino)-6-oxo-heptanoic acid methyl ester and 5-(2-methoxy-benzoylamino)-6-oxo-heptanoic acid methyl ester (3.45 g, 99%)

Sources & evidence

ORD record
ord-5654f6da8396455aae87a94acf836dd2
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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