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Syringic Acid → HCID 18464953, compound

HRID 323360
Notes
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Reaction equation

HRID 323360 reaction equation
[C:1]1([C:7]2([CH2:12][CH2:13][OH:14])[CH2:11][CH2:10][NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([O:27][CH3:28])[C:25]=1[OH:26])[C:20](O)=[O:21].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>ClCCl.CO.ClCCl>[CH3:28][O:27][C:24]1[CH:23]=[C:19]([CH:18]=[C:17]([O:16][CH3:15])[C:25]=1[OH:26])[C:20]([N:9]1[CH2:10][CH2:11][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([CH2:12][CH2:13][OH:14])[CH2:8]1)=[O:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10742Syringic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 184645642-(3-Phenylpyrrolidin-3-yl)ethanol

Product 1

HCID 18464953HCID 18464953, compound

Reagents, catalysts & solvents 2

HCID 6344
Dichloromethane
Solvent
2×
HCID 21226129Dichloromethane methanolSolvent

Procedure

Combine 3-phenyl-3-(2-hydroxyethyl)pyrrolidine (0.50 g, 2.7 mmol) (prepared by extraction from (−)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine (R,R)-di-p-anisoyltartaric acid salt) and dichloromethane (25 mL). Add 3,5-dimethoxy-4-hydroxybenzoic acid (0.55 g, 2.78 mmol), 1-hydroxybenzotriazole hydrate (0.4 g, 2.9 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.56 g, 2.9 mmol). After 18 hours, dilute the reaction mixture with dichloromethane and extract with saturated aqueous sodium bicarbonate solution and then brine. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give residue. Chromatograph the residue on silica gel eluting with methanol/dichloromethane/concentrated aqueous ammonia 1/10/0.1 to give the title compound; Rf=0.74 (silica gel, methanol/dichloromethane/concentrated aqueous ammonia 1/10/0.1)

Workup

  1. extractionextract with saturated aqueous sodium bicarbonate solution
  2. dry with materialDry the organic layer over MgSO4
  3. filtrationfilter
  4. customevaporate in vacuo
  5. customto give residue

Sources & evidence

ORD record
ord-a0d2011d62294167a1c0e380e3928a91
Source dataset
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06211199B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes