Triethylamine → HCID 131711044, compound

HRID 1678904Notes

Reaction equation

HRID 1678904 reaction equation
[CH3:1][CH2:2][C:3]([NH:5][CH:6]1[C:25](=[O:26])[N:8]2[C:9]([C:22]([OH:24])=[O:23])=[C:10]([CH2:13][S:14][C:15]3[S:16][C:17]([CH2:20][NH2:21])=[N:18][N:19]=3)[CH2:11][S:12][C@H:7]12)=[S:4].C(N(CC)CC)C.[CH3:34][N:35]=[C:36]=[O:37]>O.O1CCCC1>[CH3:1][CH2:2][C:3]([NH:5][CH:6]1[C:25](=[O:26])[N:8]2[C:9]([C:22]([OH:24])=[O:23])=[C:10]([CH2:13][S:14][C:15]3[S:16][C:17]([CH2:20][NH:21][C:36]([NH:35][CH3:34])=[O:37])=[N:18][N:19]=3)[CH2:11][S:12][C@H:7]12)=[S:4]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 131711043HCID 131711043, compound

Product 1

HCID 131711044HCID 131711044, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

7-Methylthioacetamido-3-(5-aminomethyl-1,3, 4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (1.8 g.) and triethylamine (0.8 g.) was dissolved in a mixture of water (40 ml.) and tetrahydrofuran (40 ml.). A solution of methyl isocyanate (0.46 g.) in tetrahydrofuran (10 ml.) was added dropwise to the solution at 0°-5° C, and the mixture was stirred at the same temperature for 2 hrs. The tetrahydrofuran was distilled off under reduced pressure from the reaction mixture. The residue was washed with ethyl acetate and then adjusted to pH1.0 with 10% hydrochloric acid. The precipitating crystals were collected by filtration and then washed with water to give 7-methylthioacetamido-3-[5-(3-methylureidomethyl)-1, 3,4-thiadiazol-2-yl]thiomethyl-3-cephem-4-carboxylic acid (1.96 g.). The product was suspended in water (50 ml.), and sodium bicarbonate (0.66 g.) was added to the suspension under ice-cooling to give a solution. The insoluble substance was filtered off from the solution, and the solution was adjusted to pH1.0 with 10% hydrochloric acid. The precipitating crystals were collected by filtration, washed with water to give the pure object compound. m.p. 177°-179° C (dec.).

Workup

  1. distillationThe tetrahydrofuran was distilled off under reduced pressure from the reaction mixture
  2. washThe residue was washed with ethyl acetate
  3. filtrationThe precipitating crystals were collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-733367449b6644598efe2c7aa666c3b4
Source dataset
uspto-grants-1978_03
Patent number
US04077965

Reaction notes

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