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Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → 3-[3,5-bis-(1-ethylpropoxy)-4-hydroxyphenyl]-N-(3,5-di-t-butyl-4-hydroxybenzyl)acrylamide

HRID 1792983
Notes
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Reaction equation

HRID 1792983 reaction equation
[CH2:1]([CH:3]([O:6][C:7]1[CH:8]=[C:9]([CH:20]=[CH:21][C:22]([OH:24])=O)[CH:10]=[C:11]([O:14][CH:15]([CH2:18][CH3:19])[CH2:16][CH3:17])[C:12]=1[OH:13])[CH2:4][CH3:5])[CH3:2].[NH2:25][CH2:26][C:27]1[CH:32]=[C:31]([C:33]([CH3:36])([CH3:35])[CH3:34])[C:30]([OH:37])=[C:29]([C:38]([CH3:41])([CH3:40])[CH3:39])[CH:28]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C.CCN(CC)CC.C(Cl)Cl>[CH2:16]([CH:15]([O:14][C:11]1[CH:10]=[C:9]([CH:20]=[CH:21][C:22]([NH:25][CH2:26][C:27]2[CH:28]=[C:29]([C:38]([CH3:39])([CH3:40])[CH3:41])[C:30]([OH:37])=[C:31]([C:33]([CH3:36])([CH3:35])[CH3:34])[CH:32]=2)=[O:24])[CH:8]=[C:7]([O:6][CH:3]([CH2:1][CH3:2])[CH2:4][CH3:5])[C:12]=1[OH:13])[CH2:18][CH3:19])[CH3:17]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 6010783,5-DI-Tert-butyl-4-hydroxybenzylamineHCID 69639651HCID 69639651, compound

Product 1

HCID 850975783-[3,5-bis-(1-ethylpropoxy)-4-hydroxyphenyl]-N-(3,5-di-t-butyl-4-hydroxybenzyl)acrylamideYield 50.2%

Reagents, catalysts & solvents 3

HCID 6228
Dimethylformamide
Solvent
HCID 6344DichloromethaneSolvent
HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

To the solution of 3-[3,5-bis-(1-ethylpropoxy)-4-hydroxyphenyl]acrylic acid (30 mg, 0.09 mmol) in DMF (0.2 ml) and Et3N (10 μl), was added 4-aminomethyl-2,6-di-t-butylphenol (23 mg, 0.10 mmol) at 0° C. and was added the solution of BOP (44 mg, 0.10 mmol) in CH2Cl2 (0.6 ml). The solution was stirred for 30 minutes at 0° C. and then was stirred for 2 hours at room temperature. And then CH2Cl2 was evaporated in vacuo and the obtained residue was poured into ice water. The residue was extracted with EtOAc and washed with HCl (aq) and NaHCO3 (aq). And then 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=1:5), yielding 25 mg (50%) of the title compound as a yellow solid.

Workup

  1. stirringwas stirred for 2 hours at room temperature
  2. customAnd then CH2Cl2 was evaporated in vacuo
  3. additionthe obtained residue was poured into ice water
  4. extractionThe residue was extracted with EtOAc
  5. washwashed with HCl (aq) and NaHCO3 (aq)
  6. dry with materialAnd then the 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=1:5)

Sources & evidence

ORD record
ord-7ef39f94167d459b9c350cc232bd33b7
Source dataset
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07078407B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes