Hydrochloric Acid → 2-Methyl-7-[2-hexyloxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid

HRID 1155177Notes

Reaction equation

HRID 1155177 reaction equation
[CH3:1][CH:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[N:5]2[C:11](=[O:33])[CH:12]([NH:13][C:14](=[O:32])[C:15](=[N:24][O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:16]3[N:17]=[C:18]([NH:21]C=O)[S:19][CH:20]=3)[C@H:4]2[S:3]1.Cl>CO.O1CCCC1>[CH3:1][CH:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[N:5]2[C:11](=[O:33])[CH:12]([NH:13][C:14](=[O:32])[C:15](=[N:24][O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:16]3[N:17]=[C:18]([NH2:21])[S:19][CH:20]=3)[C@H:4]2[S:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 1317125502-Methyl-7-[2-hexyloxyimino-2-(2-formylaminothiazol-4-yl)acetamido]-3-cephem-4-carboxylic acidHCID 178445233HCID 178445233, compound

Product 1

HCID 1317125512-Methyl-7-[2-hexyloxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

A solution of 2-methyl-7-[2-hexyloxyimino-2-(2-formylaminothiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid (syn isomer), which can be represented as 2-methyl-7-[2-hexyloxyimino-2-(2-formylimino-2,3-dihydrothiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid (syn isomer), (5.3 g) and concentrated hydrochloric acid (4.2 g) in a mixture of methanol (53 ml) and tetrahydrofuran (40 ml) was stirred for 2 hours at 30° C., and then evaporated to dryness. The residue was dissolved in an aqueous solution of sodium bicarbonate (500 ml) and then filtered. The filtrate was adjusted to pH 3.5 with 10% hydrochloric acid with stirring under ice-cooling and further stirred for 30 minutes at the same temperature. The precipitates were collected by filtration, washed with water and then dried to give 2-methyl-7-[2-hexyloxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid (syn isomer), which can be represented as 2-methyl-7-[2-hexyloxyimino-2-(2-imino-2,3-dihydrothiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid (syn isomer), (4.45 g).

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in an aqueous solution of sodium bicarbonate (500 ml)
  3. filtrationfiltered
  4. stirringwith stirring under ice-
  5. temperaturecooling
  6. stirringfurther stirred for 30 minutes at the same temperature
  7. filtrationThe precipitates were collected by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-555ea10cbced46a3ab6205810a22bb6f
Source dataset
uspto-grants-1981_11
Patent number
US04299829

Reaction notes

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