Formate → 2-Naphthylglycolic acid

HRID 2111505Notes

Reaction equation

HRID 2111505 reaction equation
N1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([OH:11])[C:8]([OH:10])=[O:9])[CH:2]=1.C([O-])=O>>[CH:2]1[C:8]2[C:6](=[CH:5][CH:4]=[CH:3][CH:7]=2)[CH:5]=[CH:4][C:3]=1[CH:7]([OH:11])[C:8]([OH:10])=[O:9]

Participants

3

Reactant 2

HCID 283FormateHCID 13672728alpha-Hydroxypyridine-3-acetic acid

Product 1

HCID 111381432-Naphthylglycolic acid

Procedure

(−)-3-pyridylglycolic acid This Reaction was performed in 100 mM anmonium formate buffer at pH 8. To isolate the product, the reaction mixture was filtered through a 10,000 MWCO membrane to remove enzyme and then concentrated in vacuo. 1H NMR (DMSO-d6, 500 MHz) δ 8.56 (s, 1H), 8.36 (d, J=4.57 Hz, 1H), 8.25 (s, 1H), 7.71 (m, 1H), 7.25 (dd, J=4.98, 4.80 Hz 1H), 5.45 (s, 1H). 13C NMR DMSO-d6, 125 MHz) δ 165.911, 147.862, 147.251, 139.118, 133.381, 122.746, 71.508. MS calc'd for [C7H7NO3] 153.04, found 154.0 ((MALDI TOF). ee=92% [HPLC], 84% yield, [α]20598=−65.2 (c=0.5, H2O).

Workup

  1. customTo isolate the product
  2. filtrationthe reaction mixture was filtered through a 10,000 MWCO membrane
  3. customto remove enzyme
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2293570e3c0f4dc084fdc9e048652634
Source dataset
uspto-grants-2009_04
Patent number
US07521216B2

Reaction notes

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