Ethyl Acetate → (5-methyl-2-oxo-1,3-dioxolan-4-yl)methyl (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-8-oxo-3-[(Z)-2-pyrimidin-5-ylethenyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 1886695Notes

Reaction equation

HRID 1886695 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:31]/[OH:32])/[C:8]([NH:10][C@@H:11]2[C:29](=[O:30])[N:13]3[C:14]([C:26]([O-:28])=[O:27])=[C:15](/[CH:18]=[CH:19]\[C:20]4[CH:21]=[N:22][CH:23]=[N:24][CH:25]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[Na+].Br[CH2:35][CH:36]1[CH:40]([CH3:41])[O:39][C:38](=[O:42])[O:37]1.C(OCC)(=O)C>CN(C)C(=O)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:31]/[OH:32])/[C:8]([NH:10][C@@H:11]2[C:29](=[O:30])[N:13]3[C:14]([C:26]([O:28][CH2:35][CH:36]4[CH:40]([CH3:41])[O:39][C:38](=[O:42])[O:37]4)=[O:27])=[C:15](/[CH:18]=[CH:19]\[C:20]4[CH:25]=[N:24][CH:23]=[N:22][CH:21]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 133235644-Bromomethyl-5-methyl-1,3-dioxolan-2-oneHCID 88414421sodium (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-8-oxo-3-[(Z)-2-pyrimidin-5-ylethenyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Product 1

HCID 88507429(5-methyl-2-oxo-1,3-dioxolan-4-yl)methyl (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-8-oxo-3-[(Z)-2-pyrimidin-5-ylethenyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

The compound (100 mg) of Example 16 was dissolved in N,N-dimethylacetamide (2 ml), followed by the addition of 4-bromomethyl-5-methyl-1,3-dioxolan-2-one (50 mg). They were reacted for 1 hour. Ethyl acetate (50 ml) was added. The resulting mixture was washed with water, dried over magnesium sulfate, and then concentrated under reduced pressure. Ether was added to the residue and the resulting solid was collected by filtration, whereby the title compound (15 mg) was obtained.

Workup

  1. customThey were reacted for 1 hour
  2. washThe resulting mixture was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additionEther was added to the residue
  6. filtrationthe resulting solid was collected by filtration, whereby the title compound (15 mg)
  7. customwas obtained

Sources & evidence

ORD record
ord-667de51fd586422db42d2e14883bcbe6
Source dataset
uspto-grants-1992_09
Patent number
US05151417

Reaction notes

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