Hydrochloric Acid → HCID 131713033, compound

HRID 371247Notes

Reaction equation

HRID 371247 reaction equation
[CH:1]1([O:6][N:7]=[C:8]([C:31]2[N:32]=[C:33]([NH:36]C=O)[S:34][CH:35]=2)[C:9]([NH:11][CH:12]2[C:29](=[O:30])[N:14]3[C:15]([C:26]([OH:28])=[O:27])=[C:16]([CH2:19][S:20][C:21]4[S:22][CH:23]=[N:24][N:25]=4)[CH2:17][S:18][C@H:13]23)=[O:10])[CH2:5][CH2:4][CH:3]=[CH:2]1.CO.Cl.C(=O)(O)[O-].[Na+]>O.O1CCCC1>[CH:1]1([O:6][N:7]=[C:8]([C:31]2[N:32]=[C:33]([NH2:36])[S:34][CH:35]=2)[C:9]([NH:11][CH:12]2[C:29](=[O:30])[N:14]3[C:15]([C:26]([OH:28])=[O:27])=[C:16]([CH2:19][S:20][C:21]4[S:22][CH:23]=[N:24][N:25]=4)[CH2:17][S:18][C@H:13]23)=[O:10])[CH2:5][CH2:4][CH:3]=[CH:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 516892Sodium BicarbonateHCID 131713034HCID 131713034, compound

Product 1

HCID 131713033HCID 131713033, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7-[2-(2-cyclopenten-1-yl)oxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer)(2.5 g), methanol (17.5 ml),conc.hydrochloric acid (0.88 g) and tetrahydrofuran (5.0 ml) was stirred for 1.5 hours at room temperature. To the reaction mixture were added water and a saturated aqueous solution of sodium bicarbonate so that the pH was adjusted to pH 5.0. The resulting mixture was evaporated and to the residue was added ethyl acetate. The mixture was adjusted to pH 7.5 with a saturated aqueous solution of sodium bicarbonate. The aqueous layer was separated, washed with ethyl acetate and evaporated and then the residue was adjusted to pH 3.0 with 10% hydrochloric acid. The precipitates were collected by filtration, washed with water, dried over phosphorus pentoxide under reduced pressure to give 7-[2-(2-cyclopenten-1-yl)oxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer)(2.00 g). mp. 152° to 157° C. (dec.).

Workup

  1. customThe resulting mixture was evaporated and to the residue
  2. additionwas added ethyl acetate
  3. customThe aqueous layer was separated
  4. washwashed with ethyl acetate
  5. customevaporated
  6. filtrationThe precipitates were collected by filtration
  7. washwashed with water
  8. dry with materialdried over phosphorus pentoxide under reduced pressure

Sources & evidence

ORD record
ord-d3b6211354da474d8012d7c4df958f92
Source dataset
uspto-grants-1985_07
Patent number
US04529802

Reaction notes

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