Methanol → 7-[2-(3-Hydroxyoctyl)-4-oxo-3-thiazolidinyl]heptanoic acid

HRID 1439398Notes

Reaction equation

HRID 1439398 reaction equation
C([O:4][CH:5]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:6][CH2:7][CH:8]1[N:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21]C)=[O:20])[C:11](=[O:23])[CH2:10][S:9]1)(=O)C.[OH-].[Na+].CO>C(Cl)(Cl)Cl>[OH:4][CH:5]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:6][CH2:7][CH:8]1[N:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[C:11](=[O:23])[CH2:10][S:9]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 20317394Methyl 7-[2-(3-acetyloxyoctyl)-4-oxo-3-thiazolidinyl]heptanoate

Product 1

HCID 203173917-[2-(3-Hydroxyoctyl)-4-oxo-3-thiazolidinyl]heptanoic acidYield 73%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
25 °C

Procedure

A turbid mixture of methyl 7-[2-(3-acetyloxyoctyl)-4-oxo-3-thiazolidinyl]heptanoate (785 mg., 1.89 milimole), 2.5 N aqueous sodium hydroxide (2ml.), and methanol (6 ml.) is stirred at 25° C. for 15 hours. After removing the solvents in vacuo below 50° C., the residual mass is acidified with 2 N hydrochloric acid and extracted twice with ether. The combined organic extract is washed with water, dried over magnesium sulfate, and filtered. In vacuo evaporation of the filtrate provides an oily residue which is applied to a silica gel column (20 g.) with chloroform. Elution with chloroform-acetic acid (50:1; v:v; 200 ml.) affords impure product; continued elution with the same eluant (600 ml.) provides the title compound as a pale yellow oil (494 mg., 73%); pmr (CDCl3) δ 0.90 (3H, t), 2.34 (2H, t), 2.60--3.30 (H,m), 3.30--4.00 (4H, m, containing a singlet at 3.54), 4.53--4.93 (H, m) and 7.10 (2H, broad s, D2O exchangeable). Anal. Calcd. for C18H33NO4S: C, 60.13; H, 9.25; N, 3.90. Found: C, 59.87; H, 9.11; N, 3.55.

Workup

  1. customAfter removing the solvents in vacuo below 50° C.
  2. extractionextracted twice with ether
  3. extractionThe combined organic extract
  4. washis washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customIn vacuo evaporation of the filtrate
  8. customprovides an oily residue which
  9. washElution with chloroform-acetic acid (50:1; v:v; 200 ml.)
  10. customaffords impure product
  11. washelution with the same eluant (600 ml.)

Sources & evidence

ORD record
ord-93f212ee1f8b4c80b742d5fc93833cea
Source dataset
uspto-grants-1977_11
Patent number
US04059587

Reaction notes

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