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 1283147Notes

Reaction equation

HRID 1283147 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 icebath 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 icebath and excess trifluoroacetic acid
  3. customwas removed on a rotary evaporator

Sources & evidence

ORD record
ord-b3eaeb88ef1b48d193ae0d4cc0a983d5
Source dataset
uspto-grants-1976_08
Patent number
US03974153

Reaction notes

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