Triethylamine → HCID 131713924, compound

HRID 1632759Notes

Reaction equation

HRID 1632759 reaction equation
[CH2:1]([O:9][CH:10]([CH2:13][O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:11]I)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[NH2:23][C:24]1[S:25][CH:26]=[C:27]([C:29](=[N:45][O:46][CH3:47])[C:30]([NH:32][CH:33]2[C:43](=[O:44])[N:35]3[C:36]([C:40]([OH:42])=[O:41])=[CH:37][CH2:38][S:39][C@H:34]23)=[O:31])[N:28]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>CS(C)=O>[NH2:23][C:24]1[S:25][CH:26]=[C:27]([C:29](=[N:45][O:46][CH3:47])[C:30]([NH:32][CH:33]2[C:43](=[O:44])[N:35]3[C:36]([C:40]([O:42][CH2:11][CH:10]([O:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH2:13][O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:41])=[CH:37][CH2:38][S:39][C@H:34]23)=[O:31])[N:28]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 20442205HCID 20442205, compoundHCID 1317124447-[2-(2-Amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid

Product 1

HCID 131713924HCID 131713924, compoundYield 18.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 2,3-di-n-octyloxypropyl iodide (529 mg) in dimethylsulfoxide (14 ml) was added 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 1427 mg) and triethylamine (0.52 ml) at room temperature, and stirred at 40° C. for 4 hours and at 50° C. for 4 hours. The resultant mixture was poured into ice water (200 ml), adjusted to pH 8 with an aqueous solution of sodium bicarbonate and extracted with ethyl acetate (140 ml). The extract was washed with a saturated aqueous solution of sodium chloride (50 ml) and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. After washing the residue with n-hexane (8 ml), the residue was tritulated with petroleum ether and then the precipitates were collected by filtration to give 2,3-di-n-octyloxypropyl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 160 mg), mp. 75° to 78° C.

Workup

  1. extractionextracted with ethyl acetate (140 ml)
  2. washThe extract was washed with a saturated aqueous solution of sodium chloride (50 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washAfter washing the residue with n-hexane (8 ml)
  6. filtrationthe precipitates were collected by filtration

Sources & evidence

ORD record
ord-1a8917ed9b734532afc3efd923564df3
Source dataset
uspto-grants-1984_10
Patent number
US04477447

Reaction notes

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