Acetic Acid → HCID 13563837, compound

HRID 1584006Notes

Reaction equation

HRID 1584006 reaction equation
[CH2:1]([C:11]1[CH:16]=[CH:15][N:14]=[C:13]([C:17]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26]CC)=[O:25])=[O:18])[CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].O[Li].O.C(O)(=O)C>C1COCC1.O>[CH2:1]([C:11]1[CH:16]=[CH:15][N:14]=[C:13]([C:17]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[O:18])[CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 168937Lithium hydroxide, monohydrateHCID 85528603HCID 85528603, compound

Product 1

HCID 13563837HCID 13563837, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.20 g (0.52 mmol) of 5-[[(4-decyl-2-pyridinyl)carbonyl]amino]pentanoic acid, ethyl ester prepared in Example 7, 0.05 g (1 mmol, 2 eq) of LiOH·H2O in 4 ml of THF and 1 ml of H2O was stirred at room temperature for 21 hours, then 1.5 eq of glacial acetic acid was added. The resulting solution was poured into H2O and extracted with Et2O. The organic layers were combined, poured into H2O and extracted with Et2O. The organic layers were combined, dried (Na2SO4) and concentrated in vacuo. Hexanes were added to the residue and the flask was cooled. The resulting white solid was collected, yielding 180 mg (97%) of title compound: m.p. 54°-56° C.

Workup

  1. extractionextracted with Et2O
  2. additionpoured into H2O
  3. extractionextracted with Et2O
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. additionHexanes were added to the residue
  7. temperaturethe flask was cooled
  8. customThe resulting white solid was collected

Sources & evidence

ORD record
ord-b7b9db37c263412b98f7e0f46c759bac
Source dataset
uspto-grants-1985_11
Patent number
US04555520

Reaction notes

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