m-Chloroperbenzoic acid → 2,2-dimethylpropanoyloxymethyl (6R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-methoxyimino-2-(1,3-thiazol-4-yl)acetyl]amino]-5,8-dioxo-5lambda4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 247031Notes

Reaction equation

HRID 247031 reaction equation
[CH3:1][O:2]/[N:3]=[C:4](/[C:33]1[N:34]=[CH:35][S:36][CH:37]=1)\[C:5]([NH:7][CH:8]1[C:31](=[O:32])[N:10]2[C:11]([C:20]([O:22][CH2:23][O:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])=[O:21])=[C:12]([CH2:15][O:16][C:17](=[O:19])[NH2:18])[CH2:13][S:14][C@H:9]12)=[O:6].S1[C@@H]2CC(=[O:46])N2CC=C1.ClC1C=CC=C(C(OO)=O)C=1>C(Cl)(Cl)Cl>[CH3:1][O:2]/[N:3]=[C:4](/[C:33]1[N:34]=[CH:35][S:36][CH:37]=1)\[C:5]([NH:7][CH:8]1[C:31](=[O:32])[N:10]2[C:11]([C:20]([O:22][CH2:23][O:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])=[O:21])=[C:12]([CH2:15][O:16][C:17](=[O:19])[NH2:18])[CH2:13][S:14](=[O:46])[C@H:9]12)=[O:6]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 714080692-CephemHCID 886381012,2-dimethylpropanoyloxymethyl (6R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-methoxyimino-2-(1,3-thiazol-4-yl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Product 1

HCID 886379912,2-dimethylpropanoyloxymethyl (6R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-methoxyimino-2-(1,3-thiazol-4-yl)acetyl]amino]-5,8-dioxo-5lambda4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

The product (0.2 g) obtained in Example 3, i.e. a mixture of pivaloyloxymethyl 7-[(Z)-2-methoxyimino-2-(thiazol-4-yl)acetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylate and 2-cephem isomer thereof, was dissolved in chloroform (1 ml). To this solution was added dropwise a solution of m-chloroperbenzoic acid (0.059 g) in chloroform (1 ml). The mixture was stirred for 1.5 hours at room temperature. Precipitated crystals were filtered, washed with chloroform (2 ml), and dried under reduced pressure to give the title compound (0.092 g).

Workup

  1. customPrecipitated crystals
  2. filtrationwere filtered
  3. washwashed with chloroform (2 ml)
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-03d8ee6ae4d5419ea4b60c7366d3c559
Source dataset
uspto-grants-1987_11
Patent number
US04705784

Reaction notes

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