Oxygen → 3-(Hydroxymethyl)-1-[(4-methylphenyl)sulfonyl]-3-azetidinecarboxylic acid

HRID 280817Notes

Reaction equation

HRID 280817 reaction equation
O=O.[S:3]([N:13]1[CH2:16][C:15]([CH2:19][OH:20])([CH2:17][OH:18])[CH2:14]1)([C:6]1[CH:12]=[CH:11][C:9]([CH3:10])=[CH:8][CH:7]=1)(=[O:5])=[O:4].C(=O)(O)[O-:22].[Na+]>O.[Pt]>[S:3]([N:13]1[CH2:14][C:15]([CH2:19][OH:20])([C:17]([OH:22])=[O:18])[CH2:16]1)([C:6]1[CH:7]=[CH:8][C:9]([CH3:10])=[CH:11][CH:12]=1)(=[O:4])=[O:5]

Participants

6

Reactant 3

HCID 977OxygenHCID 516892Sodium Bicarbonate2×HCID 21287788HCID 21287788, compound

Product 1

HCID 200291403-(Hydroxymethyl)-1-[(4-methylphenyl)sulfonyl]-3-azetidinecarboxylic acid

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 962WaterSolvent

Procedure

Oxygen was bubbled rapidly through a stirred mixture of N-tosyl-3,3-bishydroxymethyl azetidine (0.5 g, 0.0018 mol), sodium bicarbonate (0.155 g, 0.0018 mol) and 5% Pt/C (0.3 g) in distilled water (10 ml) at 60° C. for 15 h. Sodium bicarbonate (0.155 g, 0.0018 mol) was added to maintain pH7-8 and the reaction continued a further 5 h. After cooling, the catalyst was filtered off, washed with water and the filtrate acidified with 4N HCl. Extraction with ether (x3), drying and evaporating left a white solid. The catalyst was washed again with water and the above procedure repeated to yield further solid. The whole was recrystallised from ethanol/water to give the title product as white crystals m.p. 148°-150° C.

Workup

  1. temperatureto maintain pH7-8
  2. temperatureAfter cooling
  3. filtrationthe catalyst was filtered off
  4. washwashed with water
  5. extractionExtraction with ether (x3)
  6. customdrying
  7. customevaporating
  8. waitleft a white solid
  9. washThe catalyst was washed again with water
  10. customto yield further solid
  11. customThe whole was recrystallised from ethanol/water

Sources & evidence

ORD record
ord-c2b7733e67bc419aa79b8e9d811ef73e
Source dataset
uspto-grants-1986_05
Patent number
US04591457

Reaction notes

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