Ethyl Acetate → 1-(Ethoxycarbonyloxy)ethyl (1s,5r,6s)-2-(7-acetylimidazo[5,1-b]thiazol-2-yl)-6 ((1r)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate

HRID 1839341Notes

Reaction equation

HRID 1839341 reaction equation
[C:1]([C:4]1[N:5]=[CH:6][N:7]2[CH:11]=[C:10]([C:12]3[C@H:13]([CH3:26])[C@@H:14]4[C@@H:21]([C@H:22]([OH:24])[CH3:23])[C:20](=[O:25])[N:15]4[C:16]=3[C:17]([O-:19])=[O:18])[S:9][C:8]=12)(=[O:3])[CH3:2].[Na+].[CH2:28]([O:30][C:31]([O:33][CH:34](I)[CH3:35])=[O:32])[CH3:29].C(OCC)(=O)C>CN(C=O)C>[C:1]([C:4]1[N:5]=[CH:6][N:7]2[CH:11]=[C:10]([C:12]3[C@H:13]([CH3:26])[C@@H:14]4[C@@H:21]([C@H:22]([OH:24])[CH3:23])[C:20](=[O:25])[N:15]4[C:16]=3[C:17]([O:19][CH:28]([O:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH3:29])=[O:18])[S:9][C:8]=12)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 103771441-Iodoethyl ethyl carbonateHCID 23698608Sodium (1s,5r,6s)-2-(7-acetylimidazo[5,1-b]thiazol-2-yl)-6-((1r)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate

Product 1

HCID 233879401-(Ethoxycarbonyloxy)ethyl (1s,5r,6s)-2-(7-acetylimidazo[5,1-b]thiazol-2-yl)-6 ((1r)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylateYield 64.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-10 °C

Procedure

Sodium (1S,5R,6S)-2-(7-acetylimidazo[5,1-b]thiazol-2-yl)-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate (71.9 mg) was dissolved in 2.0 ml of DMF. 1-(Ethoxycarbonyloxy)ethyl iodide (66.3 mg) was added to the solution in an argon atmosphere at −20° C. The mixture was stirred for 2 hr while raising the temperature to −10° C. Ethyl acetate (20 ml) was added to the reaction solution. The mixture was extracted twice, followed by washing twice with 10 ml of semisaturated brine. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under the reduced pressure to a volume of 2 ml. The residue was purified by column chromatography on silica gel (chloroform:methanol=15:1) and Sephadex LH-20 (dichloromethane:methanol=1:1) in that order to give 57.4 mg of the title compound.

Workup

  1. extractionThe mixture was extracted twice
  2. washby washing twice with 10 ml of semisaturated brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under the reduced pressure to a volume of 2 ml
  6. customThe residue was purified by column chromatography on silica gel (chloroform:methanol=15:1) and Sephadex

Sources & evidence

ORD record
ord-07b7381798574007b554313996fd0fdd
Source dataset
uspto-grants-2004_01
Patent number
US06677331B2

Reaction notes

Loading…