Ethyl Acetate → HCID 20276306, compound

HRID 370603Notes

Reaction equation

HRID 370603 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].[CH:5]([O:18][C:19]([C:21]1[N:22]2[CH:25]([S:26][CH2:27][C:28]=1[CH:29](Br)[CH:30]=O)[CH:24]([NH:33][C:34](=[O:45])[CH2:35][S:36][C:37]1[CH:42]=[CH:41][C:40]([Cl:43])=[C:39]([Cl:44])[CH:38]=1)[C:23]2=[O:46])=[O:20])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>O.O1CCCC1>[NH2:1][C:2]1[S:3][C:29]([C:28]2[CH2:27][S:26][CH:25]3[N:22]([C:23](=[O:46])[CH:24]3[NH:33][C:34](=[O:45])[CH2:35][S:36][C:37]3[CH:42]=[CH:41][C:40]([Cl:43])=[C:39]([Cl:44])[CH:38]=3)[C:21]=2[C:19]([O:18][CH:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:20])=[CH:30][N:4]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 2723790ThioureaHCID 20276303HCID 20276303, compound

Product 1

HCID 20276306HCID 20276306, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of thiourea (0.054 g) in distilled water (1 cc) is added to a solution of 2-benzhydryloxycarbonyl-3-(1-bromo-2-oxoethyl)-7-(3,4-dichlorophenylthio)acetamido-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (mixture of the diastereoisomers at the substituent in the 3-position) (0.5 g) in tetrahydrofuran (10 cc), and the reaction mixture is then stirred for 17 hours at 25° C. before being poured into a mixture of distilled water (250 cc), a saturated solution of sodium bicarbonate (60 cc) and ethyl acetate (60 cc). The organic phase is washed with distilled water (3×30 cc) and then with a saturated solution of sodium chloride (30 cc) and dried over magnesium sulphate. The residue obtained after concentration of the solvent to dryness under reduced pressure (30 mm Hg; 4 kPa) at 30° C. is chromatographed on a column (height: 28 cm, diameter: 2 cm) of silica gel (0.04-0.063 mm), elution being carried out under a pressure of 0.5 bar (50 kPa) with a 30/70 by volume mixture of cyclohexane and ethyl acetate, and 15 cc fractions being collected. Fractions 7 to 10, containing the pure product, are combined and concentrated under reduced pressure (30 mm Hg; 4 kPa) at 30° C. to give 3-(2-aminothiazol-5-yl)-2-benzhydryloxycarbonyl-7-(3,4-dichlorophenylthio)acetamido-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (0.29 g) in the form of a hard, pale yellow foam.

Workup

  1. washThe organic phase is washed with distilled water (3×30 cc)
  2. dry with materialwith a saturated solution of sodium chloride (30 cc) and dried over magnesium sulphate
  3. customThe residue obtained after concentration of the solvent to dryness under reduced pressure (30 mm Hg; 4 kPa) at 30° C.
  4. customis chromatographed on a column (height: 28 cm, diameter: 2 cm) of silica gel (0.04-0.063 mm), elution
  5. additionbeing carried out under a pressure of 0.5 bar (50 kPa) with a 30/70 by volume mixture of cyclohexane and ethyl acetate, and 15 cc fractions
  6. custombeing collected
  7. additionFractions 7 to 10, containing the pure product
  8. concentrationconcentrated under reduced pressure (30 mm Hg; 4 kPa) at 30° C.

Sources & evidence

ORD record
ord-6b2c4a0896df4e69b4c52ef5a57310a8
Source dataset
uspto-grants-1985_07
Patent number
US04526962

Reaction notes

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