Hydrochloric Acid → HCID 53340061, compound

HRID 869796Notes

Reaction equation

HRID 869796 reaction equation
[C:1]([NH:22][C@@H:23]([CH2:31][CH2:32][CH2:33][CH2:34][NH:35][C:36](=[O:43])/[CH:37]=[CH:38]/[C:39]([O:41][CH3:42])=[O:40])[C:24]([O:26]C(C)(C)C)=[O:25])(=[O:21])[CH2:2][CH2:3][CH2:4]/[CH:5]=[CH:6]\[CH2:7]/[CH:8]=[CH:9]\[CH2:10]/[CH:11]=[CH:12]\[CH2:13]/[CH:14]=[CH:15]\[CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH3:20].Cl>O1CCOCC1>[C:1]([NH:22][C@@H:23]([CH2:31][CH2:32][CH2:33][CH2:34][NH:35][C:36](=[O:43])/[CH:37]=[CH:38]/[C:39]([O:41][CH3:42])=[O:40])[C:24]([OH:26])=[O:25])(=[O:21])[CH2:2][CH2:3][CH2:4]/[CH:5]=[CH:6]\[CH2:7]/[CH:8]=[CH:9]\[CH2:10]/[CH:11]=[CH:12]\[CH2:13]/[CH:14]=[CH:15]\[CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH3:20]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58348961HCID 58348961, compound

Product 1

HCID 53340061HCID 53340061, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(S)-tert-Butyl 2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenamido)-6-((E)-4-methoxy-4-oxobut-2-enamido)hexanoate (200 mg, 0.334 mmol) was taken up in 3 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 portioned 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)-2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenamido)-6-((E)-4-methoxy-4-oxobut-2-enamido)hexanoic acid. (90 mg; 50%). MS (EI) calcd for C31H46N2O6: 542.34. found 543 (M+1).

Workup

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

Sources & evidence

ORD record
ord-7be6ebf94e5741a9890de712aca72ac5
Source dataset
uspto-grants-2015_03
Patent number
US08969354B2

Reaction notes

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