Formaldehyde → HCID 60133500, compound

HRID 1026716Notes

Reaction equation

HRID 1026716 reaction equation
[OH:1][C:2]1([CH2:25][OH:26])[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][NH:20][C:21](=[O:23])[CH3:22])[O:16][C:15]3=[O:24])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.C=O.[C:29]1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[O:1]1[C:2]2([CH2:3][CH2:4][N:5]([C:8]3[CH:9]=[CH:10][C:11]([N:14]4[CH2:18][C@H:17]([CH2:19][NH:20][C:21](=[O:23])[CH3:22])[O:16][C:15]4=[O:24])=[CH:12][CH:13]=3)[CH2:6][CH2:7]2)[CH2:25][O:26][CH2:29]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 6101p-Toluenesulfonic acidHCID 68695153HCID 68695153, compound

Product 1

HCID 60133500HCID 60133500, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of (S)—N-{3-[4-(4-hydroxy-4-hydroxymethyl-piperidin-1-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (0.209 mmol), paraformaldehyde (0.233 mmol), p-toluene sulfonic acid (0.248 mmol), 4° A molecular sieves (0.160 g) in benzene (20 ml) was heated at reflux for 2 to 3 hours under stirring. The solvent was removed under vacuum to provide a residue. The residue was extracted with ethyl acetate water mixture. The combined organic layer was dried and concentrated to afford a crude product. The silica gel column chromatography afforded title compound in 57% yield.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 to 3 hours
  3. customThe solvent was removed under vacuum
  4. customto provide a residue
  5. extractionThe residue was extracted with ethyl acetate water mixture
  6. customThe combined organic layer was dried
  7. concentrationconcentrated
  8. customto afford a crude product

Sources & evidence

ORD record
ord-920bbabc01ac4ef094274e136733beb6
Source dataset
uspto-grants-2014_05
Patent number
US08729269B2

Reaction notes

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