Sodium Hydroxide → (E)-4-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidoethylamino)-4-oxobut-2-enoic acid

HRID 869783Notes

Reaction equation

HRID 869783 reaction equation
[C:1]([NH:24][CH2:25][CH2:26][NH:27][C:28](=[O:35])/[CH:29]=[CH:30]/[C:31]([O:33]C)=[O:32])(=[O:23])[CH2:2][CH2:3]/[CH:4]=[CH:5]\[CH2:6]/[CH:7]=[CH:8]\[CH2:9]/[CH:10]=[CH:11]\[CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\[CH2:21][CH3:22].[OH-].[Na+]>C1COCC1>[C:1]([NH:24][CH2:25][CH2:26][NH:27][C:28](=[O:35])/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32])(=[O:23])[CH2:2][CH2:3]/[CH:4]=[CH:5]\[CH2:6]/[CH:7]=[CH:8]\[CH2:9]/[CH:10]=[CH:11]\[CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\[CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53255264(E)-methyl 4-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidoethylamino)-4-oxobut-2-enoate

Product 1

HCID 58348972(E)-4-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidoethylamino)-4-oxobut-2-enoic acidYield 98.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(E)-Methyl 4-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidoethylamino)-4-oxobut-2-enoate (200 mg, 0.41 mmol) was taken up in 5 mL of THF along with 2 mL of a 5 N NaOH. The resulting reaction mixture was stirred at room temperature for 1 h, concentrated under reduced pressure to remove the THF, and diluted with water (10 mL). The aqueous layer was acidified to pH=2 with 3 N HCl and then extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4) and concentrated under reduced pressure to afford 190 mg of (E)-4-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidoethylamino)-4-oxobut-2-enoic acid (97% yield). MS (EI) calcd for C28H40N2O4: 468.30. found 469 (M+1).

Workup

  1. customThe resulting reaction mixture
  2. concentrationconcentrated under reduced pressure
  3. customto remove the THF
  4. additiondiluted with water (10 mL)
  5. extractionextracted with EtOAc
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-abe19ff387a7400c8e056092c059b46d
Source dataset
uspto-grants-2015_03
Patent number
US08969354B2

Reaction notes

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