Hydrochloric Acid → HCID 53340058, compound

HRID 869798Notes

Reaction equation

HRID 869798 reaction equation
[C:1]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][C@H:29]([NH:37][C:38](=[O:45])/[CH:39]=[CH:40]/[C:41]([O:43][CH3:44])=[O:42])[C:30]([O:32]C(C)(C)C)=[O:31])(=[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>O1CCOCC1>[C:1]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][C@H:29]([NH:37][C:38](=[O:45])/[CH:39]=[CH:40]/[C:41]([O:43][CH3:44])=[O:42])[C:30]([OH:32])=[O:31])(=[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 313Hydrochloric AcidHCID 58348951HCID 58348951, compound

Product 1

HCID 53340058HCID 53340058, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(S)-tert-butyl 6-((4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamido)-2-((E)-4-methoxy-4-oxobut-2-enamido)hexanoate (500 mg) was taken up in 6 mL of a 4 N HCl solution in dioxane and stirred at room temperature under an inert atmosphere of argon for 2 h. The reaction mixture was concentrated under reduced pressure and the resulting residue was partitioned between 30 mL of EtOAc and 30 mL of water. The organic layer was further washed with brine until the pH of the water layer was close to neutral, dried over Na2SO4 and concentrated under reduced pressure. Purification by preparative HPLC using a mixture of aqueous acetonitrile that has been buffered with 0.1% TFA afforded (S)-6-((4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamido)-2-((E)-4-methoxy-4-oxobut-2-enamido)hexanoic acid (160 mg; 35%). MS (EI) calcd for C33H48N2O6: 568.35. found 569 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was partitioned between 30 mL of EtOAc and 30 mL of water
  3. washThe organic layer was further washed with brine until the pH of the water layer
  4. customwas close to neutral,
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customPurification by preparative HPLC
  8. additiona mixture of aqueous acetonitrile that

Sources & evidence

ORD record
ord-898bd70b3f504e3d8c534912884b1c9c
Source dataset
uspto-grants-2015_03
Patent number
US08969354B2

Reaction notes

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