Phosphoric Acid → HCID 88783875, compound

HRID 2398132Notes

Reaction equation

HRID 2398132 reaction equation
[CH:1]([NH:3][C@@H:4]1[C:19](=[O:20])[N:6]2[C:7]([C:16]([OH:18])=[O:17])=[C:8]([CH2:11]OC(=O)C)[CH2:9][S:10][C@H:5]12)=[O:2].[CH3:21][C:22]1[S:26][C:25]([SH:27])=[N:24][N:23]=1.P(=O)(O)(O)O>P([O-])([O-])([O-])=O>[CH:1]([NH:3][C@@H:4]1[C:19](=[O:20])[N:6]2[C:7]([C:16]([OH:18])=[O:17])=[C:8]([CH2:11][S:27][C:25]3[S:26][C:22]([CH3:21])=[N:23][N:24]=3)[CH2:9][S:10][C@H:5]12)=[O:2]

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 12764266HCID 12764266, compoundHCID 178434161HCID 178434161, compound

Product 1

HCID 88783875HCID 88783875, compoundYield 31.5%

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

A solution of 7β-formamido-3-acetoxymethylceph-3-em-4-carboxylic acid (24.0 g) and 5-methyl-1,3,4-thiadiazole-2-thiol (10.56g) in M.pH 6.4 phosphate buffer (600 ml.) was heated at 60° for 41/2 hours. The solution was cooled to 20° and the pH was adjusted from 6 to 5 with phosphoric acid. The solution was extracted with ethyl acetate the pH of the aqueous layer was taken to 2 with phosphoric acid and the product was extracted into ethyl acetate. The extract was washed with brine, dired and concentrated to a low volume under reduced pressure and added to stirred petroleum. The resulting solid was collected and dried to give the title compound (9.36 g.) [α]D -98° (c 1 DMSO),λmax. (pH 6 buffer) 271 nm (ε 11,400), τ values (D2 0 + NaHCO3) include 1.74 (s;CHO), 4.30 (d, J 4.5 Hz; C-7 H), 4.88 (d, J. 4.5 Hz; C-5 H) and 7.25 (s; CH3).

Workup

  1. temperatureThe solution was cooled to 20°
  2. extractionThe solution was extracted with ethyl acetate the pH of the aqueous layer
  3. extractionthe product was extracted into ethyl acetate
  4. washThe extract was washed with brine
  5. concentrationdired and concentrated to a low volume under reduced pressure
  6. additionadded
  7. customThe resulting solid was collected
  8. customdried

Sources & evidence

ORD record
ord-b6815523a65247c1ba3365b86ed0e85d
Source dataset
uspto-grants-1977_05
Patent number
US04024134

Reaction notes

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