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Dicyclohexylcarbodiimide → HCID 85136525, compound

HRID 1792980
Notes
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Reaction equation

HRID 1792980 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH:18]=[CH:19][C:20]([OH:22])=O)[CH:9]=[C:10]([O:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:11]=1[OH:12])[CH2:2][CH2:3][CH3:4].[NH2:23][CH2:24][CH2:25][C:26]1[CH:31]=[C:30]([C:32]([CH3:35])([CH3:34])[CH3:33])[C:29]([OH:36])=[C:28]([C:37]([CH3:40])([CH3:39])[CH3:38])[CH:27]=1.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>CC#N>[CH2:14]([O:13][C:10]1[CH:9]=[C:8]([CH:18]=[CH:19][C:20]([NH:23][CH2:24][CH2:25][C:26]2[CH:31]=[C:30]([C:32]([CH3:33])([CH3:35])[CH3:34])[C:29]([OH:36])=[C:28]([C:37]([CH3:40])([CH3:39])[CH3:38])[CH:27]=2)=[O:22])[CH:7]=[C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])[C:11]=1[OH:12])[CH2:15][CH2:16][CH3:17]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 104908664-(2-Aminoethyl)-2,6-di-t-butylphenolHCID 69640036HCID 69640036, compound

Product 1

HCID 85136525HCID 85136525, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

To the solution of 3-(3,5-dibutoxy-4-hydroxyphenyl)acrylic acid (130 mg, 0.421 mmol), 4-(2-aminoethyl)-2,6-di-t-butylphenol (110 mg, 0.441 mmol) and HOBT (70 mg, 0.51 mmol) in MeCN 10 ml were DCC at 0° C. After 5 minutes, the solution was stirred for 2 hours at room temperature. And then the precipitate was removed by filtering it through a celite layer and the solution was poured into CH2Cl2. The solution was washed with 2N HCl and saturated NaHCO3 solution and the water was dried over anhydrous magnesium sulfate and filtered. The obtained filtrate was vacuum concentrated to give the residue, which was purified by column chromatography (EtOAc:Hexane=1:3), yielding 208 mg (91%) of the title compound.

Workup

  1. customat 0° C
  2. customAnd then the precipitate was removed
  3. filtrationby filtering it through a celite layer
  4. additionthe solution was poured into CH2Cl2
  5. washThe solution was washed with 2N HCl and saturated NaHCO3 solution
  6. dry with materialthe water was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give the residue, which
  10. customwas purified by column chromatography (EtOAc:Hexane=1:3)

Sources & evidence

ORD record
ord-15ed3afbed324fc5a0787f9298282063
Source dataset
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07078407B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes