Reaction #348331

ord-1e03d4f41f2a430d8536dcdecc3fdc2d

Reaction equation

CON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(CO)CS[C@H]12)c1ccco1
(6R,7R)-3-Hydroxymethyl-7-[2-(fur-2-yl)-2-methoxyiminoacetamido]ceph-3-em-4-carboxylic acid
Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O
ATP
NC(=O)OP(=O)([O-])[O-]
carbamoyl phosphate
O=S(=O)([O-])[O-].[Mg+2]
magnesium sulphate
Cl
hydrochloric acid
→
CON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(COC(N)=O)CS[C@H]12)c1ccco1
title compound
Yield 34.4%
CON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(COC(N)=O)CS[C@H]12)c1ccco1
(6R,7R)-3-Carbamoyloxymethyl-7-[2(fur-2-yl)-2-methoxyiminoacetamido]ceph-3-em-4-carboxylic acid
Yield 34.4%

Reactants

CON=C(C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(CO)CS[C@H]12)c1ccco1
(6R,7R)-3-Hydroxymethyl-7-[2-(fur-2-yl)-2-methoxyiminoacetamido]ceph-3-em-4-carboxylic acid
Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O
ATP
NC(=O)OP(=O)([O-])[O-]
carbamoyl phosphate
O=S(=O)([O-])[O-].[Mg+2]
magnesium sulphate
Cl
hydrochloric acid

Reagents

[Cl-].[Cl-].[Mn+2]
manganese chloride

Solvents

—
solution

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.WAITleft for 10 mins
  2. 2
    Extractionand extracted with ethyl acetate
  3. 3
    ExtractionThe ethyl acetate layer was back extracted with 0.1 M sodium bicarbonate which
  4. 4
    Extractionre-extracted with ethyl acetate
  5. 5
    OtherThis extract was dried under reduced pressure
  6. 6
    Otherthe solid triturated with diethyl ether

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 0-transcarbamoylase solution (50 ml) prepared in Example 8 and the final volume made up to 100 ml 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 0.1 M 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, E1 cm1% 405 (273 nm). The n.m.r. spectrum resembled that of an authentic sample of title compound.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04164447uspto-grants-1979_08