Hydrochloric Acid → HCID 86673201, compound

HRID 1746362Notes

Reaction equation

HRID 1746362 reaction equation
[C:1]([NH:24][CH2:25][CH2:26][NH:27][C:28](=[O:39])[CH2:29][N:30](C)[C:31](=O)OC(C)(C)C)(=[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].Cl.C([O-])([O-])=O.[Na+].[Na+]>CCOC(C)=O>[CH3:31][NH:30][CH2:29][C:28]([NH:27][CH2:26][CH2:25][NH:24][C:1](=[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])=[O:39]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 86673200HCID 86673200, compound

Product 1

HCID 86673201HCID 86673201, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

tert-Butyl (2-((2-((4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamido)ethyl)amino)-2-oxoethyl)(methyl)carbamate was taken up in 2 mL of EtOAc and 2 mL of saturated HCl in EtOAc was added. The resulting reaction mixture was stirred at room temperature for 2 h. Enough saturated aqueous Na2CO3 was added to adjust the pH=8. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4) and concentrated under reduced pressure to afford 530 mg of (4Z,7Z,10Z,13Z,16Z,19Z)—N-(2-(2-(methylamino)acetamido)ethyl)docosa-4,7,10,13,16,19-hexaenamide (99% yield).

Workup

  1. customThe resulting reaction mixture
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e75cfd6396d44a18b07b7bab068d14e2
Source dataset
uspto-grants-2015_10
Patent number
US09150504B2

Reaction notes

Loading…