Water → HCID 13175971, compound

HRID 2413411Notes

Reaction equation

HRID 2413411 reaction equation
[NH2:1][CH:2]1[C:9](=[O:10])[N:8]2[CH:3]1[S:4][CH2:5][C:6]([C:14]1[S:18][C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:16][CH:15]=1)=[C:7]2[C:11]([OH:13])=[O:12].O.C(=O)(O)[O-].[Na+].[S:31]1[CH:35]=[CH:34][CH:33]=[C:32]1[CH2:36][C:37](Cl)=[O:38]>CC(C)=O>[C:11]([C:7]1[N:8]2[CH:3]([S:4][CH2:5][C:6]=1[C:14]1[S:18][C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:16][CH:15]=1)[CH:2]([NH:1][C:37](=[O:38])[CH2:36][C:32]1[S:31][CH:35]=[CH:34][CH:33]=1)[C:9]2=[O:10])([OH:13])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 1623622-Thiopheneacetyl chlorideHCID 516892Sodium BicarbonateHCID 13175970HCID 13175970, compound

Product 1

HCID 13175971HCID 13175971, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
-10 °C

Procedure

A solution of 7-amino-2-carboxy-8-oxo-3-(2-phenylthiazol-5-yl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene (3.3 g) in a mixture of distilled water (35 cc) and acetone (24 cc) containing sodium bicarbonate (2 g) is cooled to -10° C. and then treated with a solution of (thien-2-yl)-acetyl chloride (0.86 cc) in acetone (10 cc), which is added dropwise in 8 minutes. The reaction mixture is stirred for 30 minutes at -10° C. and then for 3 hours at 20° C. The acetone is evaporated under reduced pressure (30 mm Hg; 4 kPa) at 30° C. and ethyl acetate (150 cc) and a saturated sodium bicarbonate solution (100 cc) are added. The aqueous layer is extracted with ethyl acetate (100 cc), then treated with decolorising charcoal (1 g) and a filtration aid (diatomaceous earth powder) (5 g), and filtered on the filtration aid, rinsing with distilled water (2×50 cc). The combined filtrates are acidified to pH 2 with 4N hydrochloric acid. The precipitate is filtered off, washed with ethyl acetate (50 cc) and then triturated with isopropyl ether (100 cc) and dried. 2-Carboxy-8-oxo-3-(2-phenyl-thiazol-5-yl)-7-(thien-2-yl-acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene (0.8 g) is obtained in the form of a cream-coloured solid.

Workup

  1. additionis added dropwise in 8 minutes
  2. waitfor 3 hours at 20° C
  3. customThe acetone is evaporated under reduced pressure (30 mm Hg; 4 kPa) at 30° C.
  4. additionethyl acetate (150 cc) and a saturated sodium bicarbonate solution (100 cc) are added
  5. extractionThe aqueous layer is extracted with ethyl acetate (100 cc)
  6. additiontreated with decolorising charcoal (1 g)
  7. filtrationa filtration aid (diatomaceous earth powder) (5 g), and filtered on the filtration aid
  8. washrinsing with distilled water (2×50 cc)
  9. filtrationThe precipitate is filtered off
  10. washwashed with ethyl acetate (50 cc)
  11. customtriturated with isopropyl ether (100 cc)
  12. customdried

Sources & evidence

ORD record
ord-9e2ed580aeba4d7bbd2f5a06a63e67aa
Source dataset
uspto-grants-1985_01
Patent number
US04496560

Reaction notes

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