Water → HCID 131722179, compound

HRID 1858528Notes

Reaction equation

HRID 1858528 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:27](=[O:28])[N:13]3[C:14]([C:24]([OH:26])=[S:25])=[C:15]([C:18]4[S:19][C:20]([CH3:23])=[N:21][N:22]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:35]([O:41][CH2:42]I)(=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37].O>CN(C)C(=O)C.C(OCC)(=O)C>[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:27](=[O:28])[N:13]3[C:14]([C:24]([O:26][CH2:42][O:41][C:35](=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37])=[S:25])=[C:15]([C:18]4[S:19][C:20]([CH3:23])=[N:21][N:22]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 104401Iodomethyl pivalateHCID 178433973HCID 178433973, compound

Product 1

HCID 131722179HCID 131722179, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 7β-(2-phenylacetamido)-3-(5-methyl-1,3,4-thiadiazol-2-yl)thio-3-cephem-4-carboxylic acid (492 mg) in N,N-dimethylacetamide (4 ml) was added cesium carbonate (200 mg) under ice-cooling, stirred at the same temperature for 1.5 hours. To the mixture was added iodomethyl pivalate (297 mg), stirred for 1 hour at the same temperature. To the mixture were added water (50 ml) and ethyl acetate (50 ml). The organic layer was separated, washed with water and saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo. The residue was triturated with diethyl ether to give pivaloyloxymethyl 7β-(2-phenylacetamido)-3-(5-methyl-1,3,4-thiadiazol-2-yl)thio-3-cephem-4-carboxylate (492 mg).

Workup

  1. temperaturecooling
  2. stirringstirred for 1 hour at the same temperature
  3. customThe organic layer was separated
  4. washwashed with water and saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-b3d0ac50022047d393deb59c7d4e0fdf
Source dataset
uspto-grants-2000_11
Patent number
US06150351

Reaction notes

Loading…