Formate → HCID 11083910, compound

HRID 964517Notes

Reaction equation

C([O-])=O.[CH3:4][C:5]([CH3:12])=[CH:6][C:7](=[O:11])[C:8]([OH:10])=[O:9].C1N=C(N)C2N=CN([C@@H]3O[C@H](COP(OP(OC[C@H]4O[C@@H](N5C=C(C(N)=O)CC=C5)[C@H](O)[C@@H]4O)(O)=O)(O)=O)[C@@H](O)[C@H]3O)C=2N=1.C([O-])=O.[Na+].P(OCC([C@H]([C@@H]([C@@H](COP(O)(O)=O)O)O)O)=O)(O)(O)=O.SC[C@H]([C@@H](CS)O)O.Cl>C(O)C(N)(CO)CO.C(OCC)(=O)C>[OH:11][C@@H:7]([CH:6]=[C:5]([CH3:12])[CH3:4])[C:8]([OH:10])=[O:9]

Participants

Conditions

Temperature: -20 °C

Procedure

MVS/GG (6 units (μ moles/minute/30° C.)) and yeast formate dehydrogenase (5 units) were added to a solution of 4-methyl-2-oxo-3-pentenoic acid (1.0 mM) in deoxygenated Tris buffer (5 mM:pH 6.0; 80 ml) containing NADH (0.02 mM), sodium formate (3.1 mM), fructose-1,6-bisphosphate (0.4 mM) and dithiothreitol (0.08 mM). The solution was stirred at room temperature (-20° C.) under nitrogen for 5 days with periodic addition of 0.2 mM HCl to maintain pH in the range of 6.0-6.2. Acidification to pH 2.0 and extractive work-up with ethyl acetate gave (S)-2-hydroxy-4-methyl-3-pentenoic acid in 91% isolated yield. Analysis of the (R)-MTPA derivative and comparison to a racemic standard gave a value of at least 99% for entantiomeric excess.

Workup

temperatureto maintain pH in the range of 6.0-6.2

Sources & evidence

ORD record: ord-b93b4ded05b04ede89ed695f252958b6
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05770410

Reaction notes

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