Hydrochloric Acid → HCID 13127783, compound

HRID 1111438Notes

Reaction equation

HRID 1111438 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][C@@H:10]1[C:22](=[O:23])[N:12]2[C:13]([C:19]([OH:21])=[O:20])=[C:14]([CH2:17]O)[CH2:15][S:16][C@H:11]12)=[O:8].[SH:24][C:25]1[N:29]([CH3:30])[N:28]=[N:27][N:26]=1.P(OC)(OC)OC.Cl>C(OCC)(=O)C.O.CCOCC>[CH3:30][N:29]1[C:25]([S:24][CH2:17][C:14]2[CH2:15][S:16][C@@H:11]3[C@H:10]([NH:9][C:7](=[O:8])[CH2:6][C:2]4[S:1][CH:5]=[CH:4][CH:3]=4)[C:22](=[O:23])[N:12]3[C:13]=2[C:19]([OH:21])=[O:20])=[N:26][N:27]=[N:28]1

Participants

8

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8472Trimethyl phosphiteHCID 930153-(Hydroxymethyl)-7-{[1-hydroxy-2-(thiophen-2-yl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidHCID 178482017HCID 178482017, compound

Product 1

HCID 13127783HCID 13127783, compoundYield 118.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
22.5 °C

Procedure

To 582 mg of 7β-[2-(2-thienyl)acetamido]-3-hydroxymethyl-3-cephem-4-carboxylic acid and 174 mg of 5-mercapto-1-methyl-1H-tetrazole was added 12 ml of ethyl acetate to make a solution. To the solution were added in sequence 0.25 ml of trimethyl phosphite and 0.2 ml of ether solution of hydrogen chloride (5mol/l), and the mixture was stirred at 20 to 25° C. for 3hours. To the reaction solution was added 10 ml of water, whose pH was adjusted to 2 with 2N HCl, which was then allowed to form two layers. The aqueous layer was taken, to which was added 10 ml of ethyl acetate. The mixture was allowed to form two layers. The organic layers were combined and washed with 5 ml of aqueous saline, which was dried over anhydrous magnesium sulfate, which was then concentrated under reduced pressure. To the concentrate was added ether, then precipitating powdery product was collected by filtration, washed and dried to give 804 mg (yield: 89%) of 3-(1-methyl-1H-tetrazol-5-yl) thiomethyl-7β-[2-(2-thienyl)acetamido]-3-cephem-4-carboxylic acid.

Workup

  1. customto form two layers
  2. customto form two layers
  3. washwashed with 5 ml of aqueous saline, which
  4. dry with materialwas dried over anhydrous magnesium sulfate, which
  5. concentrationwas then concentrated under reduced pressure
  6. additionTo the concentrate was added ether
  7. filtrationprecipitating powdery product was collected by filtration
  8. washwashed
  9. customdried

Sources & evidence

ORD record
ord-f54201e223bb4eb5959c61fe484fc5df
Source dataset
uspto-grants-1990_12
Patent number
US04980464

Reaction notes

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