Formaldehyde → L-Pantothenic acid

HRID 1391402Notes

Reaction equation

[C:1]([OH:15])(=[O:14])[CH2:2][CH2:3][NH:4][C:5](=[O:13])[C@@H:6]([C:8]([CH2:11][OH:12])([CH3:10])[CH3:9])[OH:7].CC1(C)C(O)C(=O)OC1.C=O.[C-]#N>>[C:1]([OH:15])(=[O:14])[CH2:2][CH2:3][NH:4][C:5](=[O:13])[C@H:6]([C:8]([CH2:11][OH:12])([CH3:10])[CH3:9])[OH:7]

Participants

Reactant 4

HCID 712Formaldehyde

HCID 989(+-)-Pantolactone

HCID 5975Cyanide

HCID 6613Pantothenic Acid

Product 1

HCID 5748353L-Pantothenic acid

Procedure

Pantothenic acid can be prepared by chemical synthesis, or biotechnologically by fermentation of suitable microorganisms in suitable nutrient solutions. In the chemical synthesis, DL-pantolactone is an important precursor. It is prepared in a multi-stage process from formaldehyde, isobutylaldehyde and cyanide, and in further process steps, the racemic mixture is separated, D-pantolactone is subjected to a condensation reaction with β-alanine, and D-pantothenic acid is obtained in this way.

Workup

customin further process steps, the racemic mixture is separated
customD-pantolactone is subjected to a condensation reaction with β-alanine

Sources & evidence

ORD record: ord-e8300acfe5a44cfebc4d75f95493ba60
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07338792B2

Reaction notes

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