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Methanol → HCID 21919204, compound

HRID 1245161
Notes
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Reaction equation

HRID 1245161 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:33])=[C:5]([C:24]([O:31][CH3:32])=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[CH2:6][C:7]1[C:8]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=[O:11].CO.[CH3:36]CN=C=NCCCN(C)C.Cl>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:1][O:2][C:3]1[C:4]([CH3:33])=[C:5]([C:24]([O:31][CH3:32])=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[CH2:6][C:7]1[C:8]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([O:12][CH3:36])=[O:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 887MethanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 219192093-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-benzyloxybenzoic Acid

Product 1

HCID 21919204HCID 21919204, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 6344DichloromethaneSolvent

Procedure

3-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-benzyloxybenzoic acid (652 mg, 1.4424 mmol) was dissolved in methylene chloride (20 ml), then anhydrous methanol (231 mg, 7.2187 mmol), 4-dimethylaminopyridine (264 mg, 2.1639 mmol) and WSC-HCl (830 mg, 4.3296 mmol) were added thereto and the mixture was stirred at room temperature for 16 hours. The reaction solution was washed with water and dried and the solvent was evaporated therefrom. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give the title compound (490 mg, 1.0515 mmol, 73%).

Workup

  1. washThe reaction solution was washed with water
  2. customdried
  3. customthe solvent was evaporated
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-4bdcbec7b4cf4fc59dcc6968025c1975
Source dataset
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07122543B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes