Hydrochloric Acid → (6R,7R)-3-(carbamoyloxymethyl)-7-[[2-(2-furanyl)-2-methoxyimino-1-oxoethyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 616523Notes

Reaction equation

HRID 616523 reaction equation
[OH:1][CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[C@H:13]([NH:14][C:15](=[O:25])[C:16]([C:20]3[O:21][CH:22]=[CH:23][CH:24]=3)=[N:17][O:18][CH3:19])[C:12](=[O:26])[N:7]2[C:8]=1[C:9]([OH:11])=[O:10].P(OC[C@H]1[O:45][C@@H:44]([N:46]2C3N=CN=C(N)C=3N=C2)[C@H](O)[C@@H]1O)(OP(OP(O)(O)=O)(O)=O)(=O)O.P([O-])([O-])(OC(=O)N)=O.S([O-])([O-])(=O)=O.[Mg+2].Cl>[Cl-].[Mn+2].[Cl-]>[C:44]([O:1][CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[C@H:13]([NH:14][C:15](=[O:25])[C:16]([C:20]3[O:21][CH:22]=[CH:23][CH:24]=3)=[N:17][O:18][CH3:19])[C:12](=[O:26])[N:7]2[C:8]=1[C:9]([OH:11])=[O:10])(=[O:45])[NH2:46]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 59575'-AtpHCID 24083Sulfuric acid magnesium salt (1:1)HCID 3423467Carbamic acid, monoanhydride with phosphoric acid, ion(2-)HCID 54170549(6R,7R)-3-Hydroxymethyl-7-[2-(fur-2-yl)-2-methoxyiminoacetamido]ceph-3-em-4-carboxylic acid

Product 1

HCID 41375(6R,7R)-3-(carbamoyloxymethyl)-7-[[2-(2-furanyl)-2-methoxyimino-1-oxoethyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidYield 34.4%

Reagents, catalysts & solvents 1

HCID 10313134Manganese(2+) dichlorideCatalyst

Procedure

(6R,7R)-3-Hydroxymethyl-7-[2-(fur-2-yl)-2-methoxyiminoacetamido]ceph-3-em-4-carboxylic acid (syn isomer) (40 mg), ATP (300 mg), carbamoyl phosphate (150 mg), magnesium sulphate (20 mg) and manganese chloride (20 mg) were added to a portion of the O-transcarbamoylase solution (50 ml) prepared in Example 8 and the final volume made up to 100ml at a pH of 6.75. The mixture was incubated at 28° for 3 hours and was then acidified by addition of conc. hydrochloric acid (2.5 ml), left for 10 mins. and extracted with ethyl acetate. The ethyl acetate layer was back extracted with 0.1M sodium bicarbonate which was then acidified and re-extracted with ethyl acetate. This extract was dried under reduced pressure and the solid triturated with diethyl ether to afford title compound (15.3 mg) as a dry powder, E1cm1% 405 (273 nm). The n.m.r. spectrum resembled that of an authentic sample of title compound.

Workup

  1. waitleft for 10 mins
  2. extractionand extracted with ethyl acetate
  3. extractionThe ethyl acetate layer was back extracted with 0.1M sodium bicarbonate which
  4. extractionre-extracted with ethyl acetate
  5. customThis extract was dried under reduced pressure
  6. customthe solid triturated with diethyl ether

Sources & evidence

ORD record
ord-4f1b1b98e67c49d5ab36d091b1d9c6ad
Source dataset
uspto-grants-1978_02
Patent number
US04075061

Reaction notes

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