2-Aminophenol → HCID 69640042, compound

HRID 1792985Notes

Reaction equation

HRID 1792985 reaction equation
[CH2:1]([O:7][C:8]1[CH:9]=[C:10]([CH:22]=[CH:23][C:24]([OH:26])=O)[CH:11]=[C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:13]=1[OH:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[OH:34].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]([O:15][C:12]1[CH:11]=[C:10]([CH:22]=[CH:23][C:24]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[OH:34])=[O:26])[CH:9]=[C:8]([O:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:13]=1[OH:14])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

7

Reactant 3

HCID 58012-AminophenolHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 69639720HCID 69639720, compound

Product 1

HCID 69640042HCID 69640042, compoundYield 34%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

To the solution of 3-(3,5-bishexyloxy-4-hydroxyphenyl) acrylic acid (40 mg, 0.11 mmol) in DMF (1 ml) and Et3N (17 μl), was added 2-aminophenol (13 mg, 0.12 mmol) at 0° C. and was added the solution of BOP (53 mg, 0.12 mmol) in CH2Cl2 (0.6 ml). The solution was stirred for 30 minutes at 0° C. and then was stirred for 1.5 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 17 mg (34%) of the title compound as a white solid.

Workup

  1. stirringwas stirred for 1.5 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-ea81dd70bcd34b8da3a095b9c3d2d22e
Source dataset
uspto-grants-2006_07
Patent number
US07078407B2

Reaction notes

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