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 989877Notes

Reaction equation

HRID 989877 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-3629844f9aea4f06a590cfe4328aac5e
Source dataset
uspto-grants-2002_10
Patent number
US06458780B1

Reaction notes

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