Formaldehyde → HCID 53783994, compound

HRID 2413704Notes

Reaction equation

HRID 2413704 reaction equation
[CH2:1]=O.[O:3]=[C:4]1[NH:7][C@H:6]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:5]1.[C:18](=[O:21])([OH:20])[O-:19].[Na+]>C(O)=O>[OH:19][CH2:18][N:7]1[C:4](=[O:3])[CH2:5][C@H:6]1[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].[CH:18]([O:20][CH2:1][N:7]1[C:4](=[O:3])[CH2:5][C@H:6]1[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])=[O:21]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 717310Benzyl (2S)-4-oxoazetidine-2-carboxylate

Product 2

HCID 53783994HCID 53783994, compoundHCID 54137886HCID 54137886, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To a mixture of 10 ml of formic acid and 20 ml of formalin was added 3 g of (S)-benzyl 4-oxo-2-azetidine-carboxylate (14). The resulting mixture was kept at 50° C. for 15 minutes. After cooling, the mixture was made alkaline with a saturated sodium bicarbonate aqueous solution and extracted twice with 50 ml of ether. The ethereal extracts were washed with a saturated sodium chloride aqueous solution and then dried. The solvent was removed by distillation under reduced pressure and the residue thus obtained was purified by column chromatography using silica gel. Thus, 970 mg of (S)-benzyl 1-hydroxymethyl-4-oxo-2-azetidinecarboxylate (15) and 1.78 g of (S)-benzyl 1-formyloxymethyl-4-oxo-2-azetidinecarboxylate (16) were obtained.

Workup

  1. temperatureAfter cooling
  2. extractionextracted twice with 50 ml of ether
  3. washThe ethereal extracts were washed with a saturated sodium chloride aqueous solution
  4. customdried
  5. customThe solvent was removed by distillation under reduced pressure
  6. customthe residue thus obtained
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-36ab6e7adf9c4bbeade3b2ad4b89af76
Source dataset
uspto-grants-1988_01
Patent number
US04719207

Reaction notes

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