Citric Acid → 4-(6-Carboxyhexyl)-5-(3-hydroxy-1-trans-octenyl)-thiazole

HRID 972242Notes

Reaction equation

HRID 972242 reaction equation
[C:1]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[N:12]=[CH:13][S:14][C:15]=1/[CH:16]=[CH:17]/[CH:18]([OH:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])([O:3]C)=[O:2].P([O-])([O-])([O-])=O.[Na].C[C@@H]([C@@H]1[C@@]2(C)[C@@H](O)C[C@@H]3[C@@]4(C)CC[C@@H](O)C[C@H]4C[C@@H](O)[C@H]3[C@@H]2CC1)CCC(NCCS([O-])(=O)=O)=O.[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O.C(OCC)(=O)C.CCCCCCC>[C:1]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[N:12]=[CH:13][S:14][C:15]=1/[CH:16]=[CH:17]/[CH:18]([OH:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])([OH:3])=[O:2]

Participants

9

Reactant 5

HCID 311Citric AcidHCID 1061PhosphateHCID 5360545SodiumHCID 214064094-(6-Carbomethoxyhexyl)-5-(3-hydroxy-1-trans-octenyl)-thiazoleHCID 23666345Sodium Taurocholate

Product 1

HCID 203174374-(6-Carboxyhexyl)-5-(3-hydroxy-1-trans-octenyl)-thiazoleYield 74.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×HCID 8900HeptaneSolvent

Conditions

Temperature
25 °C

Procedure

To the suspension of 1.75 g of 4-(6-carbomethoxyhexyl)-5-(3-hydroxy-1-trans-octenyl)-thiazole (Ic, R1 = H) in 35 ml of a 0.2 M phosphate buffer of pH 7.5, 175 mg of the lipase enzyme specified in Example 5, 17.5 mg of the sodium salt of taurocholic acid and 1.75 ml of a 10 % solution of gum arabic were added. The mixture was then shaken at 25° C in a screening shaker desk at 260 revolutions/minute and an amplitude of 2 cm for 24 hours, whereafter the reaction mixture was diluted with 100 ml of water, acidified with citric acid and extracted with 3 × 70 ml of ethyl acetate. The ethyl acetate extract was dried over sodium sulphate and evaporated in vacuo. The obtained 1.95 g of evaporation residue was purified by chromatography on a column prepared with 50 g of silicic acid, using mixtures of n-heptane and ethyl acetate whose ethyl acetate content was gradually increased, as the eluting solvent. 4-(6-Carboxyhexyl)-5-(3-hydroxy-1-trans-octenyl)-thiazole (ID, R1 = H) was eluted from the column by a mixture consisting of 70 % ethyl acetate and 30 % n-heptane. Thus, 1.25 g of a product of chromatographic purity was obtained which was recrystallized from a mixture of diethyl ether and n-hexane. 30

Workup

  1. additionwere added
  2. extractionextracted with 3 × 70 ml of ethyl acetate
  3. extractionThe ethyl acetate extract
  4. dry with materialwas dried over sodium sulphate
  5. customevaporated in vacuo
  6. customThe obtained 1.95 g of evaporation residue
  7. customwas purified by chromatography on a column
  8. customprepared with 50 g of silicic acid
  9. temperaturewas gradually increased, as the eluting solvent
  10. wash4-(6-Carboxyhexyl)-5-(3-hydroxy-1-trans-octenyl)-thiazole (ID, R1 = H) was eluted from the column by a mixture

Sources & evidence

ORD record
ord-c4afdc3020944a43aa8e4b112142f6c0
Source dataset
uspto-grants-1977_10
Patent number
US04052407

Reaction notes

Loading…