Hydrochloric Acid → HCID 58416605, compound

HRID 1746360Notes

Reaction equation

HRID 1746360 reaction equation
[C:1]([NH:24][CH2:25][CH2:26][NH:27]C(=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>[NH2:27][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]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 86657274HCID 86657274, compound

Product 1

HCID 58416605HCID 58416605, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

tert-Butyl 2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidoethylcarbamate (600 mg, 1.27 mmol) was taken up in 2 mL of EtOAc along with 2 mL of saturated HCl in EtOAc at 0° C. The resulting reaction mixture was stirred at room temperature for 2 h. Saturated aqueous Na2CO3 was added to adjust the pH=8. The organic layer was separated, dried (Na2SO4) and concentrated under reduced pressure to afford 470 mg of the (4Z,7Z,10Z,13Z,16Z,19Z)—N-(2-aminoethyl)docosa-4,7,10,13,16,19-hexaenamide (98% yield).

Workup

  1. customThe resulting reaction mixture
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-59b2d292e93d4bf888eed762d9a38dcc
Source dataset
uspto-grants-2015_10
Patent number
US09150504B2

Reaction notes

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