Toluene → HCID 131712077, compound

HRID 1413130Notes

Reaction equation

HRID 1413130 reaction equation
COC(C[C:6]1[CH2:7][S:8][C@@H:9]2[C@H:29]([NH:30][C:31](=[O:40])[CH2:32][O:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:28](=[O:41])[N:10]2[C:11]=1[C:12]([O:14]C(C1C=CC=CC=1)C1C=CC=CC=1)=[O:13])=O.[C:42]1([O:48][CH3:49])C=CC=C[CH:43]=1.FC(F)(F)C(O)=[O:53].C1(C)C=CC=CC=1>C(Cl)Cl>[CH3:49][O:48][C:42]([CH2:43][CH:7]1[CH:6]=[C:11]([C:12]([OH:14])=[O:13])[N:10]2[C:28](=[O:41])[C@@H:29]([NH:30][C:31](=[O:40])[CH2:32][O:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C@H:9]2[S:8]1)=[O:53]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 70560519HCID 70560519, compound

Product 1

HCID 131712077HCID 131712077, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.72 g (3 mmols) of diphenylmethyl 3-(methoxycarbonylmethyl)-7β-phenoxyacetylamino-3-cephem-4-carboxylate in 21 ml of methylene chloride are stirred with 1.62 ml (5 equivalents) of anisole and 9.3 ml (40 equivalents) of trifluoroacetic acid for 30 minutes in an ice bath, 100 ml of cold toluene are added and the mixture is evaporated in a rotary evaporator. The residue is digested with ether and the precipitate which has formed is filtered off, washed with ether and dried. A crude product is obtained and is chromatographed on 10 g of silica gel, which had been deactivated by the addition of 5% of water. Elution with methylene chloride and 20-30% of ethyl acetate gives amorphous 3-(methoxycarbonylmethyl-7β-phenoxyacetylamino-3-cephem-4-carboxylic acid, which according to thin layer chromatography is a single compound; Rf 0.38 (on silica gel; using n-butanol:acetic acid:water, 67:10:23); UV spectrum (in ethanol): λmax =262, 267 and 274; IR spectrum (in methylene chloride): bands at 2.94, 5.58,5.74, 5.88, 6.11, 6.24, 6.59 and 6.69μ.

Workup

  1. customthe mixture is evaporated in a rotary evaporator
  2. customthe precipitate which has formed
  3. filtrationis filtered off
  4. washwashed with ether
  5. customdried
  6. customA crude product is obtained
  7. customis chromatographed on 10 g of silica gel, which
  8. additionhad been deactivated by the addition of 5% of water
  9. washElution with methylene chloride and 20-30% of ethyl acetate

Sources & evidence

ORD record
ord-21aaccbc0b8c43e69d46ca71f2eb029c
Source dataset
uspto-grants-1981_02
Patent number
US04248868

Reaction notes

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