Hydrochloric Acid → 3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-7-[2-hydroxy-2-(2-mesylamino-1,3-thiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid

HRID 1659425Notes

Reaction equation

HRID 1659425 reaction equation
[CH3:1][N:2]1[C:6]([S:7][CH2:8][C:9]2[CH2:10][S:11][C@@H:12]3[CH:19]([NH:20][C:21](=[O:40])[CH:22]([O:33]C4CCCCO4)[C:23]4[N:24]=[C:25]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[S:26][CH:27]=4)[C:18](=[O:41])[N:13]3[C:14]=2[C:15]([OH:17])=[O:16])=[N:5][N:4]=[N:3]1.C(O)C.Cl.C(=O)(O)[O-].[Na+]>O>[CH3:1][N:2]1[C:6]([S:7][CH2:8][C:9]2[CH2:10][S:11][C@@H:12]3[CH:19]([NH:20][C:21](=[O:40])[CH:22]([OH:33])[C:23]4[N:24]=[C:25]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[S:26][CH:27]=4)[C:18](=[O:41])[N:13]3[C:14]=2[C:15]([OH:17])=[O:16])=[N:5][N:4]=[N:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 516892Sodium BicarbonateHCID 1317125683-(1-methyl-1H-tetrazol-5-yl)thiomethyl7-[2-(2-tetrahydropyranyl)oxy-2-(2-mesylamino-1,3-thiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid

Product 1

HCID 704906013-(1-methyl-1H-tetrazol-5-yl)thiomethyl-7-[2-hydroxy-2-(2-mesylamino-1,3-thiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 3-(1-methyl-1H-tetrazol-5-yl)thiomethyl7-[2-(2-tetrahydropyranyl)oxy-2-(2-mesylamino-1,3-thiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid, which can be represented as 3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-7-[2-(2-tetrahydropyranyl)oxy-2-(2-mesylimino-2,3-dihydro-1,3-thiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid, (0.85 g.), ethanol (15 ml.), water (5 ml.) and 2 N hydrochloric acid (5 ml.) was stirred for 2.5 hours at room temperature. After the reaction, the reaction mixture was diluted with water (20 ml.), adjusted to pH 8 with 5% sodium bicarbonate aqueous solution and then washed with diethyl ether. Thus obtained aqueous layer was adjusted to pH 4 to 5 with 10% hydrochloric acid and washed with ethyl acetate. The aqueous layer was adjusted to pH 1 to 2 with 10% hydrochloric acid and then extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solvent was distilled off from the extract, and the residue was washed in diethyl ether, collected by filtration and then dried to give pale brown powder of 3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-7-[2-hydroxy-2-(2-mesylamino-1,3-thiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid, which can be represented as 3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-7-[2-hydroxy-2-(2-mesylimino-2,3-dihydro-1,3-thiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid, (0.2 g.), mp. 120° to 146° C. (dec.).

Workup

  1. customAfter the reaction
  2. washwashed with diethyl ether
  3. washwashed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent was distilled off from the extract
  8. washthe residue was washed in diethyl ether
  9. filtrationcollected by filtration
  10. customdried

Sources & evidence

ORD record
ord-f8638b0f8d4c407dae2a989d5f47df6a
Source dataset
uspto-grants-1981_12
Patent number
US04303655

Reaction notes

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