Triethylamine → HCID 13175155, compound

HRID 2413399Notes

Reaction equation

HRID 2413399 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7](Cl)=[O:8].[C:10]([NH:13][C:14]1[S:15][C:16]([C:19]2[CH2:26][S:25][CH:24]3[N:21]([C:22](=[O:28])[CH:23]3[NH2:27])[C:20]=2[C:29]([O:31][CH:32]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])=[CH:17][N:18]=1)(=[O:12])[CH3:11].C(N(CC)CC)C>O1CCCC1>[C:10]([NH:13][C:14]1[S:15][C:16]([C:19]2[CH2:26][S:25][CH:24]3[N:21]([C:22](=[O:28])[CH:23]3[NH:27][C:7](=[O:8])[CH2:6][C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)[C:20]=2[C:29]([O:31][CH:32]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[O:30])=[CH:17][N:18]=1)(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1623622-Thiopheneacetyl chlorideHCID 13175153HCID 13175153, compound

Product 1

HCID 13175155HCID 13175155, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of (thien-2-yl)-acetyl chloride (0.55 cc) in dry tetrahydrofuran (5 cc) is added, in 5 minutes, to a solution of 3-(2-acetamido-thiazol-5-yl)-7-amino-2-benzhydryloxycarbonyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (2.27 g) in dry tetrahydrofuran (27.5 cc) at 2° C., and after 30 minutes a solution of triethylamine (0.63 cc) in dry tetrahydrofuran (5 cc) is added. After 1 hour's reaction at 2° C., the reaction mixture is filtered and the filtrate is diluted with a mixture of ethyl acetate (200 cc) and half-saturated sodium bicarbonate solution (200 cc). The organic layer is washed with water (100 cc) followed by a saturated sodium chloride solution (100 cc), dried over magnesium sulphate and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residue is chromatographed on a column (height: 30 cm; diameter: 5 cm) of silica (0.04-0.06 mm), elution being effected under 0.4 bar (40 kPa) with a 30:70 (by volume) mixture of cyclohexane and ethyl acetate, and 50 cc fractions being collected. Fractions 15 to 22, containing the pure product, are combined and concentrated under reduced pressure (30 mm Hg; 4 kPa) at 40° C. 3-(2-Acetamido-thiazol-5-yl)-2-benzhydryloxycarbonyl-8-oxo-7-(thien-2-yl-acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene (0.92 g) is obtained in the form of a yellow powder.

Workup

  1. customAfter 1 hour's reaction at 2° C.
  2. filtrationthe reaction mixture is filtered
  3. additionthe filtrate is diluted with a mixture of ethyl acetate (200 cc) and half-saturated sodium bicarbonate solution (200 cc)
  4. washThe organic layer is washed with water (100 cc)
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  7. customThe residue is chromatographed on a column (height: 30 cm; diameter: 5 cm) of silica (0.04-0.06 mm), elution
  8. additionbeing effected under 0.4 bar (40 kPa) with a 30:70 (by volume) mixture of cyclohexane and ethyl acetate, and 50 cc fractions
  9. custombeing collected
  10. additionFractions 15 to 22, containing the pure product
  11. concentrationconcentrated under reduced pressure (30 mm Hg; 4 kPa) at 40° C

Sources & evidence

ORD record
ord-40cf48533b8f4a69a0ebf7ae2e16c544
Source dataset
uspto-grants-1985_01
Patent number
US04496560

Reaction notes

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