Ammonium Chloride → HCID 88421509, compound

HRID 1197399Notes

Reaction equation

HRID 1197399 reaction equation
[Cl-].[NH4+].NC(N)=S.[NH2:7][C@:8]1([NH:40][CH:41]=[O:42])[C:38](=[O:39])[N:10]2[C:11]([C:22]([O:24][CH:25]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])=[C:12]([CH2:15]SC3SC=NN=3)[CH2:13][S:14][C@H:9]12>CN(C)C=O>[NH2:7][C@:8]1([NH:40][CH:41]=[O:42])[C:38](=[O:39])[N:10]2[CH:11]([C:22]([O:24][CH:25]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])[C:12](=[CH2:15])[CH2:13][S:14][C@H:9]12

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2723790ThioureaHCID 14431626HCID 14431626, compound

Product 1

HCID 88421509HCID 88421509, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Powdered ammonium chloride (1.25 g) and powdered thiourea (0.5 g) were added to a solution of diphenylmethyl 7β-amino-7α-formamido-3-[(1,3,4-thiadiazol-2- yl)thiomethyl]ceph-3-em-4-carboxylate in N,N-dimethylformamide (20 ml) at ca. -10° C. (ice/acetone bath) with stirring. After 5 min activated (freshly acid washed) zinc powder (1.5 g) was added in four portions over 3 min. After 25 min the mixture was filtered through Kieselguhr and the residue washed with ethyl acetate and water. Ethyl acetate (100 ml) and water (100 ml) was added to the combined filtrate and washings. The organic phase was separated and the aqueous phase re-extracted with ethyl acetate (50 ml). The combined organic extracts were washed with water (×5), then brine (×1), and dried over anhydrous magnesium sulphate, filtered and the filtrate evaporated. Purification by silica gel chromatography eluting with ethyl acetate/n-hexane furnished the title compound as a white foam (0.744 g; containing ca. 10% diphenylmethyl 7 β-amino-7α-formamido-3-methylceph-3-em).

Workup

  1. wash(freshly acid washed) zinc powder (1.5 g)
  2. additionwas added in four portions over 3 min
  3. filtrationAfter 25 min the mixture was filtered through Kieselguhr
  4. washthe residue washed with ethyl acetate and water
  5. additionEthyl acetate (100 ml) and water (100 ml) was added to the combined filtrate and washings
  6. customThe organic phase was separated
  7. extractionthe aqueous phase re-extracted with ethyl acetate (50 ml)
  8. washThe combined organic extracts were washed with water (×5)
  9. dry with materialbrine (×1), and dried over anhydrous magnesium sulphate
  10. filtrationfiltered
  11. customthe filtrate evaporated
  12. customPurification by silica gel chromatography
  13. washeluting with ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-2c43e1402b1e4509aa2e1d349ed0b85f
Source dataset
uspto-grants-1994_01
Patent number
US05275816

Reaction notes

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