Hydrochloric Acid → HCID 50991755, compound

HRID 922088Notes

Reaction equation

HRID 922088 reaction equation
[C:1]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][C@H:29]([NH:34][C:35](=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[N:38][CH:37]=1)[C:30]([O:32]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].[OH-].[Na+].Cl>C1COCC1>[C:1]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][C@H:29]([NH:34][C:35](=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[N:38][CH:37]=1)[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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58173192HCID 58173192, compound

Product 1

HCID 50991755HCID 50991755, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-Methyl 6-((4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamido)-2-(nicotinamido)hexanoate (40 mg, 0.0695 mmol) was taken up in 2 mL of THF along with 80 μL of a 5 M NaOH solution. The resulting reaction mixture was stirred at room temperature for 2 h. It was then acidified to pH 4 with 2 N HCl and then extracted with EtOAc. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure to afford 31 mg of (S)-6-((4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamido)-2-(nicotinamido)hexanoic acid. MS calculated for C34H47N3O4: 561.36. found: [M+H]+ 562.

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e70e2b55af334e85bcaf01f72ed912fb
Source dataset
uspto-grants-2016_03
Patent number
US09278136B2

Reaction notes

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