Acetic Acid → HCID 86758623, compound

HRID 2296607Notes

Reaction equation

HRID 2296607 reaction equation
[F-].C([N+:6]([CH2:15][CH2:16][CH2:17][CH3:18])([CH2:11][CH2:12]CC)[CH2:7][CH2:8][CH2:9][CH3:10])CCC.[C:19]([OH:22])(=[O:21])[CH3:20].[C:23](=O)([O-])[OH:24].[Na+].[O:28]1CCCC1>>[OH:21][C@H:19]([O:22][C:23]([C:15]1[N:6]2[CH:7]([CH:8]3[C:16]=1[CH2:17][CH2:18][CH2:10][CH2:9]3)[CH2:12][C:11]2=[O:28])=[O:24])[CH3:20]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 8028Tetrahydrofuran2×HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 86758623HCID 86758623, compoundYield 92%

Procedure

To a solution of allyl (8S,9R,10S)-10-((R)-(1-(tert-butyldimethylsilyl)oxy)ethyl)-11-oxo-1-azatricyclo-[7.2.0.03,8]undec-2-ene-2-carboxylate (405 mg;1 mmole) prepared according to the process disclosed in Example 9a in tetrahydrofuran (10 ml), 1M tetrabutylammonium fluoride solution (3 ml; 3 mmole) in tetrahydrofuran and acetic acid (0.23 ml; 4 mmole) were added. The obtained mixture was stirred for 2 hours at room temperature. Then the solution was shaken with saturated aqueous sodium hydrogencarbonate solution (10 ml) and the obtained mixture was extracted with ethyl acetate (3×15 ml). The organic phases were combined and dried with sodium sulfate, the drying agent was filtered off and the solvent was evaporated from the filtrate. (8S,9R,10S)-10-((R)-(1-hydroxyethyl)-11-oxo-1-azatricyclo-[7.2.0.03,8]undec-2-ene-2-carboxylate (267 mg; 92%) was obtained as a crude product in the form of a yellowish viscous oil.

Workup

  1. extractionthe obtained mixture was extracted with ethyl acetate (3×15 ml)
  2. dry with materialdried with sodium sulfate
  3. filtrationthe drying agent was filtered off
  4. customthe solvent was evaporated from the filtrate

Sources & evidence

ORD record
ord-3ec1d9b454804b20bf58649a09af0de2
Source dataset
uspto-grants-2002_12
Patent number
US06489318B1

Reaction notes

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