Triethylamine → HCID 20430423, compound

HRID 2413442Notes

Reaction equation

HRID 2413442 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7](Cl)=[O:8].[NH2:10][CH:11]1[C:18](=[O:19])[N:17]2[CH:12]1[S:13][CH2:14][C:15]([C:36]1[S:40][C:39]([CH2:41][C:42]3[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=3)=[N:38][CH:37]=1)=[C:16]2[C:20]([O:22][CH:23]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH:23]([O:22][C:20]([C:16]1[N:17]2[CH:12]([S:13][CH2:14][C:15]=1[C:36]1[S:40][C:39]([CH2:41][C:42]3[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=3)=[N:38][CH:37]=1)[CH:11]([NH:10][C:7](=[O:8])[CH2:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[C:18]2=[O:19])=[O:21])([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 1623622-Thiopheneacetyl chlorideHCID 516892Sodium BicarbonateHCID 13960529HCID 13960529, compound

Product 1

HCID 20430423HCID 20430423, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

Thien-2-yl-acetyl chloride (1.4 cc) is added to a solution of 7-amino-2-benzhydryloxycarbonyl-8-oxo-3-[2-(pyrid-3-ylmethyl)-thiazol-5-yl]-5-thia-1-azabicyclo [4.2.0]oct-2-ene (6.36 g) in dry tetrahydrofuran (200 cc), and triethylamine (1.58 cc) is then added. The mixture is stirred at 20° C. for 1 hour 20 minutes and is then poured into a 65:35 (by volume) mixture of ethyl acetate and a saturated sodium bicarbonate solution. The organic phase is decanted and then washed successively with distilled water (200 cc), and a saturated sodium chloride solution (200 cc) and dried over anhydrous sodium sulphate. The drying agent is filtered off and washed with ethyl acetate (10 cc) and the filtrate is concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 30° C. The residue is purified by chromatography on a column (height: 24 cm, diameter: 3 cm) of silica gel (0.05-0.2 mm), elution being carried out with ethyl acetate (2.5 liters), and 60 cc fractions being collected. Fractions 12 to 35 are combined and concentrated to dryness under reduced pressure (30 mm Hg; B 4 kPa) at 30° C. to give 2-benzhydryloxycarbonyl-8-oxo-3-[2-(pyrid-3-ylmethyl)-thiazol-5-yl]-7-(thien-2-yl-acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene (4.45 g) in the form of a yellow froth.

Workup

  1. additionis then added
  2. customThe organic phase is decanted
  3. washwashed successively with distilled water (200 cc)
  4. dry with materiala saturated sodium chloride solution (200 cc) and dried over anhydrous sodium sulphate
  5. filtrationThe drying agent is filtered off
  6. washwashed with ethyl acetate (10 cc)
  7. concentrationthe filtrate is concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 30° C
  8. customThe residue is purified by chromatography on a column (height: 24 cm, diameter: 3 cm) of silica gel (0.05-0.2 mm), elution
  9. custombeing collected
  10. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; B 4 kPa) at 30° C.

Sources & evidence

ORD record
ord-b97ad1f1f0944a07a78ee71373b2b94b
Source dataset
uspto-grants-1985_01
Patent number
US04496560

Reaction notes

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