Triethylamine → HCID 20430419, compound

HRID 2413417Notes

Reaction equation

HRID 2413417 reaction equation
[NH2:1][CH:2]1[C:9](=[O:10])[N:8]2[CH:3]1[S:4][CH2:5][C:6]([C:27]1[S:31][C:30]([S:32][CH3:33])=[N:29][CH:28]=1)=[C:7]2[C:11]([O:13][CH:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12].[S:34]1[CH:38]=[CH:37][CH:36]=[C:35]1[CH2:39][C:40](Cl)=[O:41].C(N(CC)CC)C>O1CCCC1>[CH:14]([O:13][C:11]([C:7]1[N:8]2[CH:3]([S:4][CH2:5][C:6]=1[C:27]1[S:31][C:30]([S:32][CH3:33])=[N:29][CH:28]=1)[CH:2]([NH:1][C:40](=[O:41])[CH2:39][C:35]1[S:34][CH:38]=[CH:37][CH:36]=1)[C:9]2=[O:10])=[O:12])([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1623622-Thiopheneacetyl chlorideHCID 20430448HCID 20430448, compound

Product 1

HCID 20430419HCID 20430419, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Crude 7-amino-2-benzhydryloxycarbonyl-3-(2-methylthiothiazol-5-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (3.3 g) is dissolved in tetrahydrofuran (30 cc) and is then acylated with (thien-2-yl)-acetyl chloride (0.83 cc) in the presence of triethylamine (0.94 cc) in accordance with the working method described in Example 1. The crude product obtained is chromatographed on a column (height: 30 cm; diameter: 4 cm) of silica gel (0.04-0.06 mm), elution being carried out under a pressure of 1 bar (100 kPa), with a 70:30 (by volume) mixture of cyclohexane and ethyl acetate, and 50 cc fractions being collected. Fractions 16 to 27, containing the pure product, are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 30° C., and the residue is triturated with isopropyl ether (30 cc). 2-Benzhydryloxycarbonyl-3-(2-methylthio-thiazol-5-yl)-8-oxo-7-(thien-2-yl-acetamido)-5-thia- 1-azabicyclo[4.2.0]oct-2-ene (1.6 g) is obtained in the form of a yellow solid.

Workup

  1. customThe crude product obtained
  2. customis chromatographed on a column (height: 30 cm; diameter: 4 cm) of silica gel (0.04-0.06 mm), elution
  3. additionbeing carried out under a pressure of 1 bar (100 kPa), with a 70:30 (by volume) mixture of cyclohexane and ethyl acetate, and 50 cc fractions
  4. custombeing collected
  5. additionFractions 16 to 27, containing the pure product
  6. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 30° C.
  7. customthe residue is triturated with isopropyl ether (30 cc)

Sources & evidence

ORD record
ord-f2bf36ae9ad24850a902f7f6e1fccfb6
Source dataset
uspto-grants-1985_01
Patent number
US04496560

Reaction notes

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