3,4,5-Trimethoxybenzoic Acid → HCID 59773019, compound

HRID 2220689Notes

Reaction equation

HRID 2220689 reaction equation
CO[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6]([OH:8])=O.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[C:45]([O:49][C:50]([N:52]1[CH2:56][CH2:55][CH2:54][C@H:53]1[CH2:57][NH:58][CH2:59][C:60]1[O:61][C:62]2[CH:68]=[CH:67][CH:66]=[CH:65][C:63]=2[CH:64]=1)=[O:51])([CH3:48])([CH3:47])[CH3:46]>O1CCCC1>[C:45]([O:49][C:50]([N:52]1[CH2:56][CH2:55][CH2:54][C@H:53]1[CH2:57][N:58]([CH2:59][C:60]1[O:61][C:62]2[CH:68]=[CH:67][CH:66]=[CH:65][C:63]=2[CH:64]=1)[C:6](=[O:8])[C:5]1[CH:4]=[CH:3][C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[CH:9]=1)=[O:51])([CH3:48])([CH3:46])[CH3:47]

Participants

7

Reactant 5

HCID 83573,4,5-Trimethoxybenzoic AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59772988HCID 59772988, compound

Product 1

HCID 59773019HCID 59773019, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Experimental condition analogous to Example 1, from 3,4,5-trimethoxy benzoic acid 72 mg (0.39 mmol), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride 75 mg (0.39 mmol), 1-hydroxybenzotriazole 45 mg (0.33 mmol), triethylamine 0.05 mL (0.39 mmol), and 2-(S)-{[(benzofuran-2-ylmethyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester, 100 mg (0.3 mmol) in 3 mL tetrahydrofuran. The compound was purified through silica gel chromatography elution with ethyl acetate: methanol 9:1, gave 93 mg of white oily compound.

Workup

  1. customThe compound was purified through silica gel chromatography elution with ethyl acetate: methanol 9:1

Sources & evidence

ORD record
ord-88736907c0934e18963be709a6d2b815
Source dataset
uspto-grants-2008_08
Patent number
US07417062B2

Reaction notes

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