Citric Acid → 7-(N-(4-(1-hydroxyhexyl)phenyl)acetamido)hept-5-ynoic acid

HRID 1015461Notes

Reaction equation

HRID 1015461 reaction equation
[OH-].[Li+].[OH:3][CH:4]([C:10]1[CH:15]=[CH:14][C:13]([N:16]([CH2:20][C:21]#[C:22][CH2:23][CH2:24][CH2:25][C:26]([O:28]C)=[O:27])[C:17](=[O:19])[CH3:18])=[CH:12][CH:11]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O.C1COCC1>[OH:3][CH:4]([C:10]1[CH:11]=[CH:12][C:13]([N:16]([CH2:20][C:21]#[C:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])[C:17](=[O:19])[CH3:18])=[CH:14][CH:15]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 3

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 59728277Methyl 7-(N-(4-(1-hydroxyhexyl)phenyl)acetamido)hept-5-ynoate

Product 1

HCID 597282817-(N-(4-(1-hydroxyhexyl)phenyl)acetamido)hept-5-ynoic acidYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (0.3 mL of a 0.5N solution in H2O, 0.14 mmol) was added to a solution of the ester 105 (23 mg, 0.062 mmol) in THF (0.3 mL) at 23° C. After stirring for 16 h the reaction was acidified with 10% citric acid and extracted with EtOAc. The organic portion was washed with brine twice and then dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by FCC (silica gel, 9:1 CH2Cl2/MeOH) to afford 17 mg (77%) of the acid 106.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic portion was washed with brine twice
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by FCC (silica gel, 9:1 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-78ff1e90e26a46408641db8df52ee47b
Source dataset
uspto-grants-2011_07
Patent number
US07985767B2

Reaction notes

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