Triethylamine → HCID 178468133, compound

HRID 1449191Notes

Reaction equation

HRID 1449191 reaction equation
[NH2:1][C@@H:2]1[C:26](=[O:27])[N:4]2[C:5]([C:23]([OH:25])=[O:24])=[C:6]([C:9]([CH2:19][PH:20]([OH:22])=[O:21])([S:13][C:14]3[NH:18][N:17]=[N:16][N:15]=3)[O:10][CH2:11][CH3:12])[CH2:7][S:8][C@H:3]12.C(N(CC)CC)C.[F:35][C:36]([F:45])([F:44])[CH2:37][S:38]([CH2:40][C:41](O)=[O:42])=[O:39]>CN(C)C=O>[F:35][C:36]([F:45])([F:44])[CH2:37][S:38]([CH2:40][C:41]([NH:1][C@@H:2]1[C:26](=[O:27])[N:4]2[C:5]([C:23]([OH:25])=[O:24])=[C:6]([C:9]([CH2:19][PH:20]([OH:22])=[O:21])([S:13][C:14]3[NH:18][N:17]=[N:16][N:15]=3)[O:10][CH2:11][CH3:12])[CH2:7][S:8][C@H:3]12)=[O:42])=[O:39]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 205740232-(2,2,2-Trifluoroethanesulfinyl)acetic acidHCID 178468132HCID 178468132, compound

Product 1

HCID 178468133HCID 178468133, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 4.36 g (0.01 mol) of 7β-amino-3-(1-ethoxyhydroxyphosphinylmethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid in 50 ml of dry dimethylformamide is treated with 4 ml of triethylamine and the mixture is stirred for 15 minutes at 25°. A slight excess of 0.01 mol of the activated ester of 2,2,2-trifluoroethylsulfinylacetic acid is added to the mixture and it is stirred an additional hour. The reaction mixture is evaporated to dryness and water and ethyl acetate are added to the residue. The layers are separated, the ethyl acetate layer is discarded, fresh ethyl acetate is added to the aqueous phase and it is acidified to pH 2.5 by addition of 6 N hydrochloric acid. The mixture is filtered, the layers are separated and the aqueous phase is treated with Amberlite IR-120H ionexchange resin and lyophilized to give the title compound.

Workup

  1. stirringis stirred an additional hour
  2. customThe reaction mixture is evaporated to dryness and water and ethyl acetate
  3. additionare added to the residue
  4. customThe layers are separated
  5. additionfresh ethyl acetate is added to the aqueous phase and it
  6. additionis acidified to pH 2.5 by addition of 6 N hydrochloric acid
  7. filtrationThe mixture is filtered
  8. customthe layers are separated
  9. additionthe aqueous phase is treated with Amberlite IR-120H ionexchange resin

Sources & evidence

ORD record
ord-884cfb4c62994f9b93896fd872b9f5ab
Source dataset
uspto-grants-1980_02
Patent number
US04189573

Reaction notes

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