2-Methoxybenzoic acid → HCID 69299503, compound

HRID 2196575Notes

Reaction equation

HRID 2196575 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]([CH3:24])[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:25](O)(=[O:34])[C:26]1[C:27]([O:32][CH3:33])=[CH:28][CH:29]=[CH:30][CH:31]=1.C(N=C=NC(C)C)(C)C>C(Cl)Cl>[CH3:33][O:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[C:25]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]([CH3:24])[C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1)=[O:34]

Participants

5

Reactant 3

HCID 113702-Methoxybenzoic acidHCID 12734DiisopropylcarbodiimideHCID 69299444HCID 69299444, compound

Product 1

HCID 69299503HCID 69299503, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 190 (177 mg, 0.530 mmol) and o-Anisic acid (97 mg, 0.636 mmol) in DCM (5 mL) was added drop-wise a solution of 1,3-Diisopropylcarbodiimide (0.100 mL, 0.636 mmol) in 2 mL of DCM and the resulting mixture was stirred at room temperature for 3 hours. After the usual work-up the residue was purified by flash chromatography using 4 to 6% MeOH in DCM to afford 191 (84.7 mg, 0.181 mmol, 34% yield) as a yellow oil. LRMS (ESI): calc. 467.3, found 468.2 (MH)+.

Workup

  1. customAfter the usual work-up the residue was purified by flash chromatography

Sources & evidence

ORD record
ord-17cfa341794d48559467d53a40c07843
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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