Iodomethyl pivalate → HCID 131722928, compound

HRID 382649Notes

Reaction equation

HRID 382649 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:25](=[O:26])[N:6]2[C:7]([C:22]([O-:24])=[O:23])=[C:8]([C:11]3[S:15][C:14]4=[C:16]([CH2:19][O:20][CH3:21])[N:17]=[CH:18][N:13]4[CH:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].[Na+].C(=O)([O-])O.[Na+].[C:33]([O:39][CH2:40]I)(=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35]>CN(C=O)C.C(OCC)(=O)C>[OH:1][C@@H:2]([C@H:4]1[C:25](=[O:26])[N:6]2[C:7]([C:22]([O:24][CH2:40][O:39][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])=[O:23])=[C:8]([C:11]3[S:15][C:14]4=[C:16]([CH2:19][O:20][CH3:21])[N:17]=[CH:18][N:13]4[CH:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3]

Participants

6

Reactant 3

HCID 104401Iodomethyl pivalateHCID 516892Sodium BicarbonateHCID 131722929HCID 131722929, compound

Product 1

HCID 131722928HCID 131722928, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-30 °C

Procedure

To a solution of 40 mg of sodium (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(7-methoxymethylimidazo[5,1-b]thiazol-2-yl)-1-methyl-1-carbapen-2-em-3-carboxylate in 0.6 ml of DMF was added 4.2 mg of sodium hydrogen carbonate, and the mixture was cooled to −30° C. under the atmosphere of argon. Pivaloyloxymethyl iodide (34 mg) was added, and the mixture was stirred for 1 hour, diluted with 30 ml of ethyl acetate, and washed with 20 ml of saturated aqueous saline and 20 ml of semi-saturated squeous saline. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to a volume of about 1 ml. The concentrate was purified by column chromatography on silica gel (chloroform:methanol=95:5) to give the title compound was obtained in a yield of 18.4 mg.

Workup

  1. washwashed with 20 ml of saturated aqueous saline and 20 ml of semi-saturated squeous saline
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure to a volume of about 1 ml
  4. customThe concentrate was purified by column chromatography on silica gel (chloroform:methanol=95:5)

Sources & evidence

ORD record
ord-c1c7cffbae5e415697d77e017ed7cb75
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Reaction notes

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