Ethanol → HCID 86740184, compound

HRID 370601Notes

Reaction equation

HRID 370601 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([C:10]2CO[CH:15]3[N:12]([C:13](=[O:23])[CH:14]3[C:18]3[S:19][CH:20]=[CH:21][CH:22]=3)[C:11]=2[NH:24][C:25](=[O:43])[CH2:26][C:27]([O:29]C(C2C=CC=CC=2)C2C=CC=CC=2)=[O:28])=[CH:8][N:9]=1)(=[O:3])[CH3:2].[CH2:44]([OH:46])[CH3:45]>C(O)=O>[C:1]([NH:4][C:5]1[S:6][C:7]([C:10]2[CH2:45][C:44](=[O:46])[CH:15]3[N:12]([C:13](=[O:23])[CH:14]3[C:18]3[S:19][CH:20]=[CH:21][CH:22]=3)[C:11]=2[NH:24][C:25](=[O:43])[CH2:26][C:27]([OH:29])=[O:28])=[CH:8][N:9]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 702EthanolHCID 86739897HCID 86739897, compound

Product 1

HCID 86740184HCID 86740184, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 3-(2-acetylaminothiazol-5-yl)-2-benzhydryloxycarbonyl-8-oxo-7-(thien-2-yl)-acetamido-5-oxa-1-azabicyclo[4.2.0]oct-2-ene (0.1 g) in formic acid (5 cc) is heated at 50° C. for 30 minutes, with stirring. The mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 50° C. and the residue is dissolved in ethanol (5 cc). The suspension obtained is stirred at 50° C. for 5 minutes and the solvent is evaporated off under reduced pressure (30 mm Hg; 4 kPa) at 50° C.; this operation is repeated once and the residue thus obtained is taken up in ethanol (2 cc). After filtration, the suspended solid gives 3-(2-acetylaminothiazol-5-yl)-2-carboxy-8-oxo-7-(thien-2-yl)-acetamido-5-oxo-1-azabicyclo[4.2.0]oct-2-ene (12 mg) in the form of a beige powder.

Workup

  1. concentrationThe mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 50° C.
  2. dissolutionthe residue is dissolved in ethanol (5 cc)
  3. customThe suspension obtained
  4. stirringis stirred at 50° C. for 5 minutes
  5. customthe solvent is evaporated off under reduced pressure (30 mm Hg; 4 kPa) at 50° C.
  6. customthe residue thus obtained
  7. filtrationAfter filtration

Sources & evidence

ORD record
ord-7721a99bcb344a97b90b6e00eb6370c0
Source dataset
uspto-grants-1985_07
Patent number
US04526962

Reaction notes

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