monoMethyl succinate → Adipic Acid

HRID 1282410Notes

Reaction equation

C[O:2][C:3](=[O:10])[CH2:4]CCCC#N.[CH3:11][O:12][C:13](=[O:19])[CH2:14][CH2:15][C:16]([OH:18])=[O:17]>P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[CH3:11][O:12][C:13](=[O:19])[CH2:14][CH2:15][CH2:16][CH2:4][C:3]([OH:10])=[O:2].[C:3]([OH:10])(=[O:2])[CH2:4][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17]

Participants

Conditions

Temperature: 25 °C

Procedure

Into a 10-mL volumetric flask was added 1.425 g (10.0 mmol, 1.00 M) of 5-cyanopentanoic acid methyl ester, 8.38 mL of potassium phosphate buffer (50 mM, pH 7.0), and 0.20 mL of a 50 wt % cell suspension (0.10 g wet cell weight, 0.024 g dry cell weight) of Acidovorax facilis 72W (ATCC 55746) cells in 0.35 M potassium phosphate buffer (pH 7.0, previously heat-treated at 50° C. for 1 h), and the resulting 10 mL suspension stirred at 25° C. Samples (0.100 mL) were withdrawn and mixed with 0.900 mL of distilled water, centrifuged, then 0.180 mL of the 1:10 diluted supernatant was mixed with 0.020 mL of 0.750 M N-methylpropionamide (HPLC external standard solution). The resulting solution was analyzed by HPLC. After 120 h, the conversion of 5-cyanopentanoic acid methyl ester was complete, and the yield (determined by HPLC) of hexanedioic acid monomethyl ester and hexanedioic acid were 97%, and 3%, respectively, with no production of 5-cyanopentanoic acid.

Workup

additionInto a 10-mL volumetric flask was added
customSamples (0.100 mL) were withdrawn
additionmixed with 0.900 mL of distilled water
addition0.180 mL of the 1:10 diluted supernatant was mixed with 0.020 mL of 0.750 M N-methylpropionamide (HPLC external standard solution)

Sources & evidence

ORD record: ord-9533cef9850e4d3a8ebcbc328fa2acea
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06455730B1

Reaction notes

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