1-Iodoethyl cyclohexyl carbonate → HCID 131727999, compound

HRID 1799705Notes

Reaction equation

HRID 1799705 reaction equation
[CH:1]1([O:7][C:8]([O:10][CH:11](I)[CH3:12])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH:14][CH2:15][CH2:16][O:17][CH2:18][C:19]1[N:20]=[CH:21][S:22][C:23]=1/[CH:24]=[CH:25]\[S:26][C:27]1[C@H:28]([CH3:41])[C@@H:29]2[C@@H:36]([C@H:37]([OH:39])[CH3:38])[C:35](=[O:40])[N:30]2[C:31]=1[C:32]([O-:34])=[O:33].[Na+]>CCCCCC.CN(C)C(=O)C>[OH:14][CH2:15][CH2:16][O:17][CH2:18][C:19]1[N:20]=[CH:21][S:22][C:23]=1/[CH:24]=[CH:25]\[S:26][C:27]1[C@H:28]([CH3:41])[C@@H:29]2[C@@H:36]([C@H:37]([OH:39])[CH3:38])[C:35](=[O:40])[N:30]2[C:31]=1[C:32]([O:34][CH:11]([O:10][C:8]([O:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:9])[CH3:12])=[O:33]

Participants

5

Reactant 2

HCID 111092781-Iodoethyl cyclohexyl carbonateHCID 23668431HCID 23668431, compound

Product 1

HCID 131727999HCID 131727999, compoundYield 20,969.6%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolvent2×HCID 31374DimethylacetamideSolvent

Procedure

A solution (2 ml) of 0.147 mg of 1-(cyclohexyloxycarbonyloxy)ethyl iodide in hexane was added to a solution of 51.8 mg of sodium (1R,5S,6S)-2-[[(Z)-2-[4-(2-hydroxyethoxy)methylthiazol-5-yl]ethen-1-yl]thio]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate in 2 ml of N,N-dimethylacetamide under an argon atmosphere at −10° C. The mixture was stirred at the same temperature for one hr, and 2 ml of hexane was then added to the reaction solution, followed by separation into an upper layer and a lower layer. Brine was added to the lower layer, and the mixture was extracted twice with ethyl acetate. The organic layers were combined, were washed twice with brine, were dried over anhydrous magnesium sulfate, were filtered, and were concentrated under the reduced pressure, and the residue was purified by column chromatography on silica gel (chloroform:methanol=20:1) to give 61.7 mg of the title compound.

Workup

  1. customfollowed by separation into an upper layer
  2. additionBrine was added to the lower layer
  3. extractionthe mixture was extracted twice with ethyl acetate
  4. washwere washed twice with brine
  5. dry with materialwere dried over anhydrous magnesium sulfate
  6. filtrationwere filtered
  7. concentrationwere concentrated under the reduced pressure
  8. customthe residue was purified by column chromatography on silica gel (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-0a17e58e3766481da80d5bbab5f6c1fc
Source dataset
uspto-grants-2013_01
Patent number
US08344154B2

Reaction notes

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