Chloroform → 7-{2-[4-(4-Fluorophenoxy)-3-hydroxybutyl]-1,1,4-trioxo-3-thiazolidinyl}heptanoic Acid

HRID 867098Notes

Reaction equation

HRID 867098 reaction equation
C([O:8][CH:9]([CH2:36][O:37][C:38]1[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=1)[CH2:10][CH2:11][CH:12]1[N:16]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25]CC2C=CC=CC=2)=[O:24])[C:15](=[O:33])[CH2:14][S:13]1(=[O:35])=[O:34])C1C=CC=CC=1.C(Cl)(Cl)Cl>C(O)C.C(OCC)(=O)C>[F:44][C:41]1[CH:40]=[CH:39][C:38]([O:37][CH2:36][CH:9]([OH:8])[CH2:10][CH2:11][CH:12]2[N:16]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[C:15](=[O:33])[CH2:14][S:13]2(=[O:34])=[O:35])=[CH:43][CH:42]=1

Participants

4

Reactant 2

HCID 6212ChloroformHCID 20317381Benzyl 7-{2-(3-benzyloxy-4-[4-fluorophenoxy]butyl)-1,1,4-trioxo-3-thiazolidinyl}heptanoate

Product 1

HCID 203173897-{2-[4-(4-Fluorophenoxy)-3-hydroxybutyl]-1,1,4-trioxo-3-thiazolidinyl}heptanoic Acid

Reagents, catalysts & solvents 1

HCID 21584252Ethanol ethylacetateSolvent

Procedure

A solution of benzyl 7-{2-[3-benzyloxy-4-(4-fluorophenoxy)butyl]-1,1,4-trioxo-3-thiazolidinyl}heptanoate (1.1 g., 1.76 millimole) in absolute ethanol-ethyl acetate (100:2; v:v; 102 ml.) is magnetically stirred and hydrogenated at 25° C. and atmospheric pressure in the presence of 10% palladium/charcoal until hydrogen consumption ceases (~139 ml. of hydrogen is consumed). After removing the catalyst by filtration, the filtrate is concentrated in vacuo leaving an oily residue which is applied to a silica gel column (20 g.) with chloroform. Impurities are eluted with chloroform-acetic acid (25:1; v:v; 200 ml.); continued elution with the same eluant (375 ml.) affords the title compound as a tlc homogeneous, viscous oil (0.59 g., 75%); pmr (CDCl3) δ2.31 (2H, t), 2.73-3.37 (H, m), 3.60-4.30 (6H, m, containing singlets at 3.80 and 3.90), 4.61 (H, t), 6.67-7.60 (6H, m, containing a broad singlet at 7.30).

Workup

  1. customhydrogenated at 25° C.
  2. customatmospheric pressure in the presence of 10% palladium/charcoal until hydrogen consumption ceases (~139 ml. of hydrogen is consumed)
  3. customAfter removing the catalyst
  4. filtrationby filtration
  5. concentrationthe filtrate is concentrated in vacuo
  6. customleaving an oily residue which
  7. washImpurities are eluted with chloroform-acetic acid (25:1; v:v; 200 ml.)
  8. washelution with the same eluant (375 ml.)

Sources & evidence

ORD record
ord-4114448d18d34190abae84f385b005a0
Source dataset
uspto-grants-1978_07
Patent number
US04102888

Reaction notes

Loading…