Formaldehyde → HCID 90457267, compound

HRID 625885Notes

Reaction equation

HRID 625885 reaction equation
[CH2:1]=O.[CH:3]1[C:15]2[CH:14]([CH2:16][O:17][C:18]([NH:20][C@@H:21]([CH2:25][O:26][C:27]3[CH:28]=[C:29]([CH3:33])[CH:30]=[CH:31][CH:32]=3)[C:22]([OH:24])=[O:23])=[O:19])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH:6]=[CH:5][CH:4]=1>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:23]=[C:22]1[O:24][CH2:1][N:20]([C:18]([O:17][CH2:16][CH:14]2[C:15]3[CH:3]=[CH:4][CH:5]=[CH:6][C:7]=3[C:8]3[C:13]2=[CH:12][CH:11]=[CH:10][CH:9]=3)=[O:19])[C@H:21]1[CH2:25][O:26][C:27]1[CH:28]=[C:29]([CH3:33])[CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 90456922HCID 90456922, compound

Product 1

HCID 90457267HCID 90457267, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

Using a Dean-Stark setup, a mixture containing paraformaldehyde (340 mg, 11.34 mmol), (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(m-tolyloxy)propanoic acid (789 mg, 1.890 mmol), and p-toluenesulfonic acid (32.5 mg, 0.189 mmol) was refluxed in Toluene (15 mL) for 2 hrs. The reaction was then cooled to RT, washed with sat. sodium bicarbonate solution, followed by brine, dried with MgSO4, filtered and concentrated to get the product (S)-(9H-fluoren-9-yl)methyl 5-oxo-4-((m-tolyloxy)methyl)oxazolidine-3-carboxylate (812 mg, 1.891 mmol, 100% yield) as a yellow oil. ESI-MS(+) m/z=430 (M+H).

Workup

  1. washwashed with sat. sodium bicarbonate solution
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c3326fb8ec294e0c99417d6782b7b893
Source dataset
uspto-grants-2016_04
Patent number
US09308236B2

Reaction notes

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