Oxalic Acid → HCID 178526186, compound

HRID 1607811Notes

Reaction equation

HRID 1607811 reaction equation
C([O:3][C:4](=[S:26])[CH2:5][CH2:6][CH2:7][C:8]#[C:9][CH2:10][C:11]#[C:12][CH2:13][C:14]#[C:15][CH2:16][C:17]#[C:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)C.P([O-])([O-])(O)=O.[Na+].[Na+].P([O-])(O)(O)=O.[K+].O1CCCCC1OC1CCCCO1.C(O)(=O)C(O)=O>C(OCC)(=O)C>[C:20]1([CH2:19][C:18]#[C:17][CH2:16][C:15]#[C:14][CH2:13][C:12]#[C:11][CH2:10][C:9]#[C:8][CH2:7][CH2:6][CH2:5][C:4]([OH:3])=[S:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 971Oxalic AcidHCID 263182Tetrahydropyranyl etherHCID 71312623Disodium hydrogenphosphate potassium dihydrogenphosphateHCID 8674338916-Phenylthiohexadeca-5,8,11,14-tetraynoic acid ethyl ester

Product 1

HCID 178526186HCID 178526186, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.7 g of 16-phenylthiohexadeca-5,8,11,14-tetraynoic acid ethyl ester, 184 ml of the pH 6.7 buffer solution of disodium hydrogen phosphate/potassium dihydrogen phosphate, prepared as in Example 1 and 17.5 g of Sigma Lipase, Type VII, from Candida cylindracea was sonicated for 5 hours at room temperature. The reaction mixture was then transferredto a separatory funnel with ethyl acetate (200 ml) and acidified with saturated solution of oxalic acid. The organic phase was separated and combined with ethyl acetate extracts of the aqueous phase. The ethyl acetate was dried over sodium sulfate and removed under vacuo. The residuewas purified by TLC on silica gel using a Chromatotron using hexane:ethyl acetate:acetic acid (60:40:1) as the eluant. The crude product was crystallized from methylene chloride-hexane, to yield 16-phenylthiohexadeca-5,8,11,14-tetraynoic acid. M.P. 69°-71° C. (dec), which was stored in dry ice.

Workup

  1. customfrom Candida cylindracea was sonicated for 5 hours at room temperature
  2. customThe organic phase was separated
  3. dry with materialThe ethyl acetate was dried over sodium sulfate
  4. customremoved under vacuo
  5. customThe residuewas purified by TLC on silica gel using a Chromatotron
  6. customThe crude product was crystallized from methylene chloride-hexane

Sources & evidence

ORD record
ord-85715dc01ff14ac89bfa6e6910266b41
Source dataset
uspto-grants-1989_09
Patent number
US04867915

Reaction notes

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