Phosphoric Acid → (6R,7R)-3-Hydroxymethyl-7-[2-(fur-2-yl)-2-methoxyiminoacetamido]ceph-3-em-4-carboxylic acid

HRID 1283719Notes

Reaction equation

HRID 1283719 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[N:27][O:28][CH3:29])[C:7]([NH:9][C@@H:10]1[C:25](=[O:26])[N:12]2[C:13]([C:22]([OH:24])=[O:23])=[C:14]([CH2:17][O:18]C(=O)C)[CH2:15][S:16][C@H:11]12)=[O:8].[OH-].[Na+].P(=O)(O)(O)O.[Cl-].[Na+]>O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[N:27][O:28][CH3:29])[C:7]([NH:9][C@@H:10]1[C:25](=[O:26])[N:12]2[C:13]([C:22]([OH:24])=[O:23])=[C:14]([CH2:17][OH:18])[CH2:15][S:16][C@H:11]12)=[O:8]

Participants

6

Reactant 4

HCID 1004Phosphoric AcidHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 71719(6R,7R)-3-Acetoxymethyl-7-[2-methoxyimino-2-(fur-2-yl) acetamido]ceph-3-em-4-carboxylic acid

Product 1

HCID 54170549(6R,7R)-3-Hydroxymethyl-7-[2-(fur-2-yl)-2-methoxyiminoacetamido]ceph-3-em-4-carboxylic acidYield 69.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A reaction mixture consisting of (6R,7R)-7-[2-(fur-2-yl)-2-methoxyiminoacetamido]-3-acetoxymethylceph-3-em-4-carboxylic acid (syn isomer) (8.0 g), sodium hydroxide (2.6 g), demineralised water (120 ml), orthophosphoric acid (2.2 ml) and a slurry (18 ml) of Rhodosporidium toruloides CBS14 prepared as in (a) above was incubated at 25°C on an orbital shaker. After 20 hr. it was shown by t.l.c. (silica gel plates with 0.5M sodium chloride as solvent) that the reaction was complete. The reaction mixture was centrifuged, and the supernatant decanted and filtered through an asbestos pad. Methyl isobutyl ketone (14 ml) was added to the clear filtrate, the mixture was magnetically stirred and a 20% solution of orthophosphoric acid was added dropwise until the pH was 2.0. The mixture was then allowed to settle, the lower aqueous layer pipetted off and the solvent layer containing a copious white precipitate was vacuum filtered. The precipitate was washed with methyl isobutyl ketone (10 ml) and ice cold water (2 × 10 ml). The product was then sucked dry and dried in vacuo at room temperature to yield title compound (5.01 g). IR and NMR spectra of the product were consistent with it being title compound. The purity was estimated to be 92.2% by HPLC.

Workup

  1. customabove was incubated at 25°C on an orbital shaker
  2. customthe supernatant decanted
  3. filtrationfiltered through an asbestos pad
  4. additionMethyl isobutyl ketone (14 ml) was added to the clear filtrate
  5. additiona 20% solution of orthophosphoric acid was added dropwise until the pH was 2.0
  6. additionthe solvent layer containing a copious white precipitate
  7. filtrationfiltered
  8. washThe precipitate was washed with methyl isobutyl ketone (10 ml) and ice cold water (2 × 10 ml)
  9. customThe product was then sucked dry
  10. customdried in vacuo at room temperature

Sources & evidence

ORD record
ord-aa12c49452884e5590924032f01f6096
Source dataset
uspto-grants-1976_08
Patent number
US03976546

Reaction notes

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