Formaldehyde → HCID 54167440, compound

HRID 1378695Notes

Reaction equation

HRID 1378695 reaction equation
C=O.[C:3](B)#N.[Na].C(#N)C.[F:10][C:11]1[CH:12]=[C:13]([N:25]2[CH2:29][C@H:28]([CH2:30][NH:31][C:32](=[O:34])[CH3:33])[O:27][C:26]2=[O:35])[CH:14]=[CH:15][C:16]=1[N:17]1[CH2:22][CH2:21][CH:20]([NH:23][CH3:24])[CH2:19][CH2:18]1>CO>[CH3:24][N:23]([CH3:3])[CH:20]1[CH2:19][CH2:18][N:17]([C:16]2[CH:15]=[CH:14][C:13]([N:25]3[CH2:29][C@H:28]([CH2:30][NH:31][C:32](=[O:34])[CH3:33])[O:27][C:26]3=[O:35])=[CH:12][C:11]=2[F:10])[CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 6342AcetonitrileHCID 20726135HCID 20726135, compoundHCID 101953985CID 101953985

Product 1

HCID 54167440HCID 54167440, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Formaldehyde (37% aq. sol., 0.4 ml) and sodium cyanoboron hydride (138 mg) were successively added to an acetonitrile suspension (3 ml) of 400 mg of the (S)-N-{3-[3-fluoro-4-(4-methylamino-piperidin-1-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (Compound No. 70) which was synthesized in Example 18, and the mixture was stirred at room temperature for 48 h. Methanol was added and the mixture was stirred for 10 min. Thereafter, alumina (5 g) was added and the residue was evaporated under vacuum. The residue was purified by alumina column chromatography (solvent: chloroform/methanol=100/1) to afford the title compound (363 mg) in a yield of 87%.

Workup

  1. customwas synthesized in Example 18
  2. stirringthe mixture was stirred for 10 min
  3. additionThereafter, alumina (5 g) was added
  4. customthe residue was evaporated under vacuum
  5. customThe residue was purified by alumina column chromatography (solvent: chloroform/methanol=100/1)

Sources & evidence

ORD record
ord-a09e035700084084a6939816d4c835c7
Source dataset
uspto-grants-1997_09
Patent number
US05668286

Reaction notes

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