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Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → HCID 86589094, compound

HRID 1792981
Notes
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Reaction equation

HRID 1792981 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].N[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.F[P-](F)(F)(F)(F)F.[N:48]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:52]2C=CC=C[C:51]=2N=N1>CN(C=O)C.CCN(CC)CC.C(Cl)Cl>[CH2:14]([O:13][C:10]1[CH:9]=[C:8]([CH:18]=[CH:19][C:20]([NH:48][CH2:52][CH2:51][CH2:24][CH2:25][C:26]2[CH:31]=[C:30]([C:32]([CH3:33])([CH3:34])[CH3:35])[C:29]([OH:36])=[C:28]([C:37]([CH3:39])([CH3:40])[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate2×HCID 104908664-(2-Aminoethyl)-2,6-di-t-butylphenolHCID 69640036HCID 69640036, compound

Product 1

HCID 86589094HCID 86589094, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 6228
Dimethylformamide
Solvent
HCID 6344DichloromethaneSolvent
HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

To the solution of 3-(3,5-dibutoxy-4-hydroxyphenyl) acrylic acid (53 mg, 0.17 mmol) in DMF (0.76 ml) and Et3N (39 μl), was added 4-(2-aminoethyl)-2,6-di-t-butylphenol (50 mg, 0.19 mmol) at 0° C. The obtained solution was added with the solution of benzotriazol-1-yloxytris (dimethylamino) phosphonium hexafluorophosphate (84 mg, 0.19 mmol) in CH2Cl2 (1 ml). The solution was stirred for 30 minutes at 0° C. and then was stirred for 12 hours at room temperature. The solution was added with BOP (70 mg, 0.16 mmol) and was stirred for 1 hour. 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=1:2), yielding 51 mg (91%) of the title compound as a brown oil.

Workup

  1. stirringwas stirred for 12 hours at room temperature
  2. stirringwas stirred for 1 hour
  3. customAnd then CH2Cl2 was evaporated in vacuo
  4. additionthe obtained residue was poured into ice water
  5. extractionThe residue was extracted with EtOAc
  6. washwashed with HCl (aq) and NaHCO3 (aq)
  7. dry with materialAnd then the water was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give the residue, which
  11. customwas purified by column chromatography (EtOAc:Hexane=1:2)

Sources & evidence

ORD record
ord-9510d77d582b450d883ef78c542b5bab
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