Methanol → (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(2-oxopyrrolidin-3-yl)oxyiminoacetic acid

HRID 414802Notes

Reaction equation

HRID 414802 reaction equation
C([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:30]/[O:31][CH:32]2[CH2:36][CH2:35][NH:34][C:33]2=[O:37])/[C:27]([OH:29])=[O:28])[N:25]=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CO>O>[NH2:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:30]/[O:31][CH:32]2[CH2:36][CH2:35][NH:34][C:33]2=[O:37])/[C:27]([OH:29])=[O:28])[N:25]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 13335553(2Z)-2-(2-oxopyrrolidin-3-yl)oxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acid

Product 1

HCID 13536827(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(2-oxopyrrolidin-3-yl)oxyiminoacetic acidYield 60.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

49 g of (Z)-2-(2-tritylaminothiazol-4-yl)-2-[(2-pyrrolidon-3-yl)oxyimino]acetic acid are suspended in a solution of one liter of methanol containing 40 ml of water, and the suspension is refluxed for 2 hours with heating. After cooling, crystalline precipitates are collected by filtration, and the crystals are washed with ethyl acetate. The crystals are recrystallized from a mixture of 500 ml of methanol and 50 ml of water, and dried at 70° C. under reduced pressure. 15.7 g of (Z)-2-(2-aminothiazol-4-yl)-2-[(2-pyrrolidon-3-yl)oxyimino]acetic acid are obtained as colorless prisms. The physico-chemical properties of this product are identical with those of the product obtained in Example 2-(4).

Workup

  1. temperaturethe suspension is refluxed for 2 hours
  2. temperaturewith heating
  3. temperatureAfter cooling
  4. customcrystalline precipitates
  5. filtrationare collected by filtration
  6. washthe crystals are washed with ethyl acetate
  7. customThe crystals are recrystallized from a mixture of 500 ml of methanol and 50 ml of water
  8. customdried at 70° C. under reduced pressure

Sources & evidence

ORD record
ord-1e14a20fc96f429da5d5f423068cbdf8
Source dataset
uspto-grants-1988_12
Patent number
US04794186

Reaction notes

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