HCID 21474427, compound → HCID 21474323, compound

HRID 2294258Notes

Reaction equation

HRID 2294258 reaction equation
C([O:8][C:9]1[C:10](=[O:30])[CH:11]=[C:12]([C:27]([OH:29])=[O:28])[N:13]([CH2:24][CH2:25]O)[C:14]=1[CH:15]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)[OH:16])C1C=CC=CC=1>CO.[Pd]>[F:23][C:20]1[CH:21]=[CH:22][C:17]([CH:15]([OH:16])[C:14]2[N:13]3[C:12]([C:27](=[O:28])[O:29][CH2:25][CH2:24]3)=[CH:11][C:10](=[O:30])[C:9]=2[OH:8])=[CH:18][CH:19]=1

Participants

4

Reactant 1

HCID 21474427HCID 21474427, compound

Product 1

HCID 21474323HCID 21474323, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

0.266 g of 5-benzyloxy-6-[(4-fluoro-phenyl)-hydroxy-methyl]-1-(2-hydroxy-ethyl)-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid are dissolved in 20 ml of methanol and hydrogenated at room temperature over 0.05 g of palladium on carbon (5%) until 1 mol of H2 per mol of starting material has been taken up. The catalyst is removed by filtration and the flitrate is concentrated to dryness by evaporation using a rotary evaporator. Recrystallisation from methanol yields 6-[(4-fluoro-phenyl)-hydroxy-methyl]-7-hydroxy-3,4-dihydro-pyrido[2,1-c]-[1,4]oxazine-1,8-dione in the form of colourless crystals. M.p.: 221°-225° C.

Workup

  1. customThe catalyst is removed by filtration
  2. concentrationthe flitrate is concentrated to dryness by evaporation
  3. customa rotary evaporator
  4. customRecrystallisation from methanol

Sources & evidence

ORD record
ord-61bdc984fed54d0bb31519711a455f89
Source dataset
uspto-grants-1997_11
Patent number
US05688815

Reaction notes

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