HCID 86739901, compound → HCID 86739900, compound

HRID 2413439Notes

Reaction equation

HRID 2413439 reaction equation
C([O:14][C:15]([CH2:17][C:18]([NH:20][C:21]1[N:22]2[CH:25]([S:26][CH2:27][C:28]=1[C:29]1[S:33][C:32]([NH:34][C:35](=[S:47])[CH2:36][CH2:37][CH2:38][NH:39]C(OC(C)(C)C)=O)=[N:31][CH:30]=1)[CH:24]([S:48][C:49]1[CH:54]=[CH:53][C:52]([Cl:55])=[C:51]([Cl:56])[CH:50]=1)[C:23]2=[O:57])=[O:19])=[O:16])(C1C=CC=CC=1)C1C=CC=CC=1>C(O)=O>[NH2:39][CH2:38][CH2:37][CH2:36][C:35]([NH:34][C:32]1[S:33][C:29]([C:28]2[CH2:27][S:26][CH:25]3[N:22]([C:23](=[O:57])[CH:24]3[S:48][C:49]3[CH:54]=[CH:53][C:52]([Cl:55])=[C:51]([Cl:56])[CH:50]=3)[C:21]=2[NH:20][C:18](=[O:19])[CH2:17][C:15]([OH:16])=[O:14])=[CH:30][N:31]=1)=[S:47]

Participants

3

Reactant 1

HCID 86739901HCID 86739901, compound

Product 1

HCID 86739900HCID 86739900, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 2-benzhydryloxycarbonyl-3-[2-(2-t-butoxycarbonylamino-ethylthioacetamido)-thiazol-5-yl]-7-(3,4-dichlorophenylthio)-acetamido-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (1.7 g) in formic acid (50 cc) is heated at 50° C. for 30 minutes and then concentrated to dryness under reduced pressure (2 mm Hg; 0.27 kPa) at 40° C. The oil which remains is taken up in acetone (20 cc), which is concentrated to dryness under reduced pressure (40 mm Hg; 5.3 kPa) at 50° C.; this operation is repeated once more and the residue is then taken up in boiling acetone (20 cc). The mixture is filtered hot and the solid collected is washed with acetone (20 cc) and ethyl ether (20 cc), to give 3-[2-(2-aminoethylthioacetamido)-thiazol-5-yl]-2-carboxy-7-(3,4-dichlorophenylthio)-acetamido-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (1.15 g) in the form of a yellow solid.

Workup

  1. concentrationconcentrated to dryness under reduced pressure (2 mm Hg; 0.27 kPa) at 40° C
  2. concentrationwhich is concentrated to dryness under reduced pressure (40 mm Hg; 5.3 kPa) at 50° C.
  3. filtrationThe mixture is filtered hot
  4. customthe solid collected
  5. washis washed with acetone (20 cc) and ethyl ether (20 cc)

Sources & evidence

ORD record
ord-fe7bbdba2a9a492192566d34e6e3bf1c
Source dataset
uspto-grants-1985_01
Patent number
US04496560

Reaction notes

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