Glyoxylic Acid → (2S,3S,4S)-4-bromo-2-fluoro-3,5-bis(benzyloxy)pentanal

HRID 716116Notes

Reaction equation

C(O)(=O)C=[O:3].CON=[CH:9][C@H:10]([F:31])[C@H:11]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C@@H:12]([Br:22])[CH2:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(OCC)(=O)C.O>O1CCCC1>[Br:22][C@@H:12]([CH2:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C@@H:11]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C@H:10]([F:31])[CH:9]=[O:3]

Participants

Conditions

Temperature: 70 °C

Procedure

3.3 mL of a 50% glyoxylic acid aqueous solution was added to a solution of 662 mg of the (2S,3S,4S)-4-bromo-2-fluoro-3,5-bis(benzyloxy)pentanal O-methyloxime in 6.6 mL of tetrahydrofuran, and the obtained mixture was then stirred at 70° C. for 4.83 hours. Thereafter, ethyl acetate and water were added to the reaction mixture. The organic layer was fractionated, and it was washed with a sodium hydrogen carbonate aqueous solution, and was then dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure, so as to obtain 655 mg of colorless oily (2S,3S,4S)-4-bromo-2-fluoro-3,5-bis(benzyloxy)pentanal and a water adduct thereof.

Workup

washit was washed with a sodium hydrogen carbonate aqueous solution
dry with materialwas then dried over anhydrous magnesium sulfate
distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record: ord-77bc70c6d0b245059c0a55710e1fa2c0
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187514B2

Reaction notes

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