Citric Acid → 2-Methyl-4-(6-carboxyhexyl)-5-(3-keto-1-trans-octenyl)-thiazole

HRID 972240Notes

Reaction equation

HRID 972240 reaction equation
[CH3:1][C:2]1[S:3][C:4](/[CH:17]=[CH:18]/[C:19](=[O:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15]C)=[O:14])[N:6]=1.[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>P([O-])([O-])([O-])=O.O>[CH3:1][C:2]1[S:3][C:4](/[CH:17]=[CH:18]/[C:19](=[O:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])[N:6]=1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 5360545SodiumHCID 214064192-Methyl-4-(6-carbomethoxyhexyl)-5-(3-keto-1-trans-octenyl)-thiazoleHCID 23666345Sodium Taurocholate

Product 1

HCID 214064272-Methyl-4-(6-carboxyhexyl)-5-(3-keto-1-trans-octenyl)-thiazoleYield 73.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1061PhosphateSolvent

Conditions

Temperature
25 °C

Procedure

To a suspension of 912 mg of 2-methyl-4-(6-carbomethoxyhexyl)-5-(3-keto-1-trans-octenyl)-thiazole (Ia, R1 = CH3) in 20 ml of 0.2 M phosphate buffer of pH 7.5, 90 mg of the lipase enzyme specified in Example 5, 9 mg of the sodium salt of taurocholic acid nd 0.9 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. Then the reaction mixture was diluted with 50 ml of water, acidified with citric acid and extracted with 3 × 40 ml of ethyl acetate. The ethyl acetate extract was dried over sodium sulphate and evaporated in vacuo. The obtained 1.03 g of evaporation residue were purified by preparative thin layer chromatography in the way specified in Example 6. Thus, 645 mg of 2-methyl-4-(6-carboxyhexyl)-5-(3-keto-1-trans-octenyl)-thiazole Ib, R1 = CH3) were obtained.

Workup

  1. additionwere added
  2. extractionextracted with 3 × 40 ml of ethyl acetate
  3. extractionThe ethyl acetate extract
  4. dry with materialwas dried over sodium sulphate
  5. customevaporated in vacuo
  6. customThe obtained 1.03 g of evaporation residue
  7. customwere purified by preparative thin layer chromatography in the way

Sources & evidence

ORD record
ord-5b34a1255a3749fa9f826d1972d228d4
Source dataset
uspto-grants-1977_10
Patent number
US04052407

Reaction notes

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