1-Iodoethyl isopropyl carbonate → 1-(isopropoxycarbonyloxy)ethyl (5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-3-yl)-1-carbapen-2-em-3-carboxylate

HRID 382645Notes

Reaction equation

HRID 382645 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:21](=[O:22])[N:6]2[C:7]([C:18]([O-:20])=[O:19])=[C:8]([C:10]3[N:11]4[CH:17]=[N:16][CH:15]=[C:12]4[S:13][CH:14]=3)[CH2:9][C@H:5]12)[CH3:3].[Na+].[CH:24]([O:27][C:28]([O:30][CH:31](I)[CH3:32])=[O:29])([CH3:26])[CH3:25]>CN(C=O)C>[OH:1][C@@H:2]([C@H:4]1[C:21](=[O:22])[N:6]2[C:7]([C:18]([O:20][CH:31]([O:30][C:28]([O:27][CH:24]([CH3:26])[CH3:25])=[O:29])[CH3:32])=[O:19])=[C:8]([C:10]3[N:11]4[CH:17]=[N:16][CH:15]=[C:12]4[S:13][CH:14]=3)[CH2:9][C@H:5]12)[CH3:3]

Participants

4

Reactant 2

HCID 110106451-Iodoethyl isopropyl carbonateHCID 131722921sodium (5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-3-yl)-1-carbapen-2-em-3-carboxylate

Product 1

HCID 1317229221-(isopropoxycarbonyloxy)ethyl (5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-3-yl)-1-carbapen-2-em-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of 48 mg of sodium (5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-3-yl)-1-carbapen-2-em-3-carboxylate in 1 ml of DMF was added 73 mg of 1-(isopropoxycarbonyloxy)ethyl iodide under the atmosphere of argon at −20° C., and the mixture was stirred for 3 hours during which the temperature was raised up to −10° C. The reaction mixture was extracted twice with 20 ml of ethyl acetate, and washed twice with 10 ml of semi-saturated aqueous saline. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to a volume of 2 ml. The residue thus obtained was purified by column chromatography on silica gel (chloroform:methanol=9:1) and on Sephadex LH-20 (dichloromethane:methanol=1:1) in this sequence to give the title compound in a yield of 22 mg.

Workup

  1. extractionThe reaction mixture was extracted twice with 20 ml of ethyl acetate
  2. washwashed twice with 10 ml of semi-saturated aqueous saline
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure to a volume of 2 ml
  6. customThe residue thus obtained
  7. customwas purified by column chromatography on silica gel (chloroform:methanol=9:1) and on Sephadex

Sources & evidence

ORD record
ord-6819e12470d840b18716080c960d07be
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Reaction notes

Loading…