N,N-Diethylaniline → HCID 178494258, compound

HRID 866886Notes

Reaction equation

HRID 866886 reaction equation
C([O:5][C:6]([C:8]1[N:13]2[C:14](=[O:19])[C@:15]([NH2:18])([O:16][CH3:17])[C@H:12]2[S:11][CH2:10][C:9]=1[CH:20]([S:28][C:29]1[NH:33][N:32]=[N:31][N:30]=1)[CH2:21][CH2:22][NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[O:7])(C)(C)C.C(N(CC)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)C>C(Cl)Cl>[C:15]([NH:18][C@:15]1([O:16][CH3:17])[C:14](=[O:19])[N:13]2[C:8]([C:6]([OH:5])=[O:7])=[C:9]([CH:20]([S:28][C:29]3[NH:30][N:31]=[N:32][N:33]=3)[CH2:21][CH2:22][NH:23][S:24]([CH3:27])(=[O:25])=[O:26])[CH2:10][S:11][C@H:12]12)(=[O:16])[C@@H:14]([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[OH:19]

Participants

4

Reactant 2

HCID 7061N,N-DiethylanilineHCID 178494282HCID 178494282, compound

Product 1

HCID 178494258HCID 178494258, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.04 g (2 mmol) of 7β-amino-7α-methoxy-3-[1-(2-methanesulfonamidoethyl)tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid t-butyl ester and 0.30 g (2 mmol) of N,N-diethylaniline in 100 ml of dry methylene chloride is stirred at 0°-5° while 0.56 g (2 mmol) of D-O-dichloroacetylmandeloyl chloride in 10 ml of methylene chloride is added dropwise over 10 minutes. The mixture is stirred in the cold for 30 minutes when warmed to room temperature and stirred for an additional 30 minutes. The solution is washed with 50 ml of cold dilute hydrochloric acid and 50 ml of cold 5% aqueous sodium bicarbonate, dried and evaporated to dryness. The residue is dissolved in a mixture of 10 ml of trifluoroacetic acid and 2 ml of m-dimethoxybenzene and stirred at ambient temperature for 2 hours. The excess trifluoroacetic acid is evaporated under vacuum and the residue is partitioned between 50 ml of ether and 50 ml of water and adjusted to pH 9.3-9.5 with 5% aqueous sodium carbonate. The organic phase is separated and discarded. The aqueous phase is stirred at pH 9.3-9.5 for 30 minutes, extracted with 50 ml of ethyl acetate which is discarded, layered with fresh ethyl acetate and adjusted to pH 1.5 with dilute hydrochloric acid. The aqueous layer is extracted with three 50 ml portions of ethyl acetate and the combined extracts are dried and evaporated to a small volume. Petroleum ether is added dropwise to precipitate the title compound which is collected by filtration and dried.

Workup

  1. additionis added dropwise over 10 minutes
  2. stirringstirred for an additional 30 minutes
  3. washThe solution is washed with 50 ml of cold dilute hydrochloric acid and 50 ml of cold 5% aqueous sodium bicarbonate
  4. customdried
  5. customevaporated to dryness
  6. dissolutionThe residue is dissolved in a mixture of 10 ml of trifluoroacetic acid and 2 ml of m-dimethoxybenzene
  7. stirringstirred at ambient temperature for 2 hours
  8. customThe excess trifluoroacetic acid is evaporated under vacuum
  9. customthe residue is partitioned between 50 ml of ether and 50 ml of water
  10. customThe organic phase is separated
  11. stirringThe aqueous phase is stirred at pH 9.3-9.5 for 30 minutes
  12. extractionextracted with 50 ml of ethyl acetate which
  13. extractionThe aqueous layer is extracted with three 50 ml portions of ethyl acetate
  14. customthe combined extracts are dried
  15. customevaporated to a small volume
  16. additionPetroleum ether is added dropwise
  17. customto precipitate the title compound which
  18. filtrationis collected by filtration
  19. customdried

Sources & evidence

ORD record
ord-85d1fe8844ad4967930324bb69f4f965
Source dataset
uspto-grants-1978_07
Patent number
US04101656

Reaction notes

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