Anisole → (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 1390408Notes

Reaction equation

HRID 1390408 reaction equation
C1(OC)C=CC=CC=1.[C:9]([O:12][CH2:13][C:14]1[CH2:15][S:16][C@@H:17]2[C@H:37]([NH:38][C:39](=[O:49])[C:40]([C:44]3[O:45][CH:46]=[CH:47][CH:48]=3)=[N:41][O:42][CH3:43])[C:36](=[O:50])[N:18]2[C:19]=1[C:20]([O:22]C(C1C=CC=CC=1)C1C=CC=CC=1)=[O:21])(=[O:11])[NH2:10]>FC(F)(F)C(O)=O>[C:9]([O:12][CH2:13][C:14]1[CH2:15][S:16][C@@H:17]2[C@H:37]([NH:38][C:39](=[O:49])[C:40]([C:44]3[O:45][CH:46]=[CH:47][CH:48]=3)=[N:41][O:42][CH3:43])[C:36](=[O:50])[N:18]2[C:19]=1[C:20]([OH:22])=[O:21])(=[O:11])[NH2:10]

Participants

4

Reactant 2

HCID 7519AnisoleHCID 54120521Diphenylmethyl 3-carbamoyloxymethyl-7beta-[2-methoxyimino-2-(fur-2-yl)acetamido]-ceph-3-em-4-carboxylate

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 97.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Trifluoroacetic acid (20 ml) was added slowly to a mixture of anisole (5 ml) and diphenylmethyl (6R,7R)-3-carbamoyloxymethyl-7-[2-(fur-2-yl)-2-methoxyiminoacetamido]ceph-3-em-4-carboxylate (syn isomer) (4.7 g, 8 mmole) which had been cooled in an ice-bath. The flask was shaken occasionally during the next 10 minutes to ensure complete solution of the solid. It was then removed from the ice-bath and excess trifluoroacetic acid was removed on a rotary evaporator. Trituration of the residue with ethyl acetate (5 ml) gave (6R,7R)-3-carbamoyloxymethyl-7-[2-(fur-2-yl)-2-methoxyiminoacetamido]ceph-3-em-4-carboxylic acid (syn isomer) (3.3 g, 94%) as a solid which was filtered off and washed with diethyl ether.

Workup

  1. temperaturehad been cooled in an ice-bath
  2. customIt was then removed from the ice-bath and excess trifluoroacetic acid
  3. customwas removed on a rotary evaporator

Sources & evidence

ORD record
ord-5bb925272c1c43e38c511fed130e28b0
Source dataset
uspto-grants-1979_02
Patent number
US04138555

Reaction notes

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