Ammonium formate → HCID 89894011, compound

HRID 925427Notes

Reaction equation

HRID 925427 reaction equation
C([O:8][CH2:9][C@H:10]1[O:14][C:13](=[O:15])[N:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:11]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[OH:8][CH2:9][C@H:10]1[O:14][C:13](=[O:15])[N:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[CH2:11]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 89893962HCID 89893962, compound

Product 1

HCID 89894011HCID 89894011, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

A solution of (S)-tert-butyl 5-(benzyloxymethyl)-2-oxooxazolidin-3-ylcarbamate (1.537 g, 4.77 mmol) in ethanol (25 mL), with 10% Pd/C (0.761 g, 0.715 mmol), was hydrogenated for 18 h at 40 psi. Conversion was about 40%. Catalyst was filtered away and replaced with fresh 10% Pd/C (0.254 g, 0.238 mmol); ammonium formate (0.752 g, 11.92 mmol) was added and the reaction was refluxed, under nitrogen, while stirring for 5 h. Conversion was complete. Catalyst was filtered away and the solvent evaporated. The residue was triturated with hot diisopropyl ether/MeOH (10:1) and left to precipitate on standing at r.t., The title compound was obtained as a white solid (802 mg, 3.45 mmol). Yield=72%.

Workup

  1. filtrationCatalyst was filtered away
  2. temperaturethe reaction was refluxed, under nitrogen
  3. filtrationCatalyst was filtered away
  4. customthe solvent evaporated
  5. customThe residue was triturated with hot diisopropyl ether/MeOH (10:1)
  6. waitleft
  7. customto precipitate
  8. customon standing at r.t.

Sources & evidence

ORD record
ord-7c6dd812a3754e7f9464b38a28e64ead
Source dataset
uspto-grants-2016_03
Patent number
US09284306B2

Reaction notes

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