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

HRID 638459Notes

Reaction equation

HRID 638459 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:37]C=O)[C:23]4[N:24]=[C:25]([NH:28][C:29]([O:31][C:32]([CH2:35][CH3:36])([CH3:34])[CH3:33])=[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)(O)[O-].[Na+]>[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:37])[C:23]4[N:24]=[C:25]([NH:28][C:29]([O:31][C:32]([CH2:35][CH3:36])([CH3:34])[CH3:33])=[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

4

Reactant 2

HCID 887058213-(1-methyl-1H-tetrazol-5-yl)thiomethyl-7-[2-formyloxy-2-(2-tert-pentyloxycarbonylamino-1,3-thiazol-4-yl)-acetamido]-3-cephem-4-carboxylic acidHCID 178447167HCID 178447167, compound

Product 1

HCID 704900803-(1-methyl-1H-tetrazol-5-yl)thiomethyl-7-[2-hydroxy-2-(2-tert-pentyloxycarbonylamino-1,3-thiazol-4-yl)-acetamido]-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-7-[2-formyloxy-2-(2-tert-pentyloxycarbonylamino-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-formyloxy-2-(2-tert-pentyloxycarbonylimino-2,3-dihydro-1,3-thiazol-4-yl)-acetamido]-3-cephem-4-carboxylic acid, (1.49 g.) and 5% sodium bicarbonate aqueous solution (100 ml.) was allowed to stand for 6 hours. After the reaction, the reaction mixture was washed with ethyl acetate. To the reaction mixture was added ethyl acetate, and the mixture was adjusted to pH 7 with dilute hydrochloric acid and then the aqueous layer was separated. To the aqueous layer was added ethyl acetate, and the mixture was adjusted to pH 1 to 2 with dilute hydrochloric acid, and the ethyl acetate layer was separated. The remaining aqueous layer was subjected to salting-out and then extracted with ethyl acetate. The ethyl acetate layer and the ethyl acetate extract were combined together, washed with water, dried over magnesium sulfate, and then the solvent was distilled off. To the residue (2.0 g.) was added diethyl ether, and the mixture was stirred for overnight, 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-tert-pentyloxycarbonylamino-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-tert-pentyloxycarbonylimino-2,3-dihydro-1,3-thiazol-4-yl)-acetamido]-3-cephem-4-carboxylic acid, (0.90 g.).

Workup

  1. customAfter the reaction
  2. washthe reaction mixture was washed with ethyl acetate
  3. additionTo the reaction mixture was added ethyl acetate
  4. customthe aqueous layer was separated
  5. additionTo the aqueous layer was added ethyl acetate
  6. customthe ethyl acetate layer was separated
  7. extractionextracted with ethyl acetate
  8. extractionThe ethyl acetate layer and the ethyl acetate extract
  9. washwashed with water
  10. dry with materialdried over magnesium sulfate
  11. distillationthe solvent was distilled off
  12. additionTo the residue (2.0 g.) was added diethyl ether
  13. filtrationcollected by filtration
  14. customdried

Sources & evidence

ORD record
ord-2092845acf6244b8a382819650bae29b
Source dataset
uspto-grants-1985_12
Patent number
US04560765

Reaction notes

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