4-Aminobenzyl alcohol → HCID 70926492, compound

HRID 1746364Notes

Reaction equation

HRID 1746364 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][CH:3]=1.[C:10](O)(=[O:32])[CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\[CH2:21]/[CH:22]=[CH:23]\[CH2:24]/[CH:25]=[CH:26]\[CH2:27]/[CH:28]=[CH:29]\[CH2:30][CH3:31].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl.[NH4+].[Cl-]>[OH:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:10](=[O:32])[CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\[CH2:21]/[CH:22]=[CH:23]\[CH2:24]/[CH:25]=[CH:26]\[CH2:27]/[CH:28]=[CH:29]\[CH2:30][CH3:31])=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 693314-Aminobenzyl alcoholHCID 445580DoconexentHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 70926492HCID 70926492, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

(4-Aminophenyl)methanol (1 mmol) was taken up in 15 mL of CH2Cl2 along with (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid (1 mmol) and HATU (1.1 mmol). The resulting reaction mixture was stirred at room temperature for 6 h and diluted with saturated aqueous NH4Cl. The two layers were separated and the organic layer was washed with brine, dried (Na2SO4) and concentrated under reduced pressure. Purification by silica gel chromatography (95% CH2Cl2, 5% MeOH) afforded (4Z,7Z,10Z,13Z,16Z,19Z)—N-(4-(hydroxymethyl)phenyl)docosa-4,7,10,13,16,19-hexaenamide.

Workup

  1. customThe resulting reaction mixture
  2. customThe two layers were separated
  3. washthe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customPurification by silica gel chromatography (95% CH2Cl2, 5% MeOH)

Sources & evidence

ORD record
ord-809f626d763d4a11afb5de2678cb55ac
Source dataset
uspto-grants-2015_10
Patent number
US09150504B2

Reaction notes

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