Sulfuric Acid → (3R,4S,5R)-4-amino-3-(1-ethyl-propoxy)-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester

HRID 492258Notes

Reaction equation

HRID 492258 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH2:11][C@@H:10]([O:12][S:13]([CH3:16])(=[O:15])=[O:14])[C@@H:9]([NH:17]P(OCC)(OCC)=O)[C@H:8]([O:26][CH:27]([CH2:30][CH3:31])[CH2:28][CH3:29])[CH:7]=1)=[O:5])[CH3:2].S(=O)(=O)(O)O.[OH-].[Na+].[NH4+].[OH-]>CCOC(C)=O.O.CCO>[CH2:1]([O:3][C:4]([C:6]1[CH2:11][C@@H:10]([O:12][S:13]([CH3:16])(=[O:14])=[O:15])[C@@H:9]([NH2:17])[C@H:8]([O:26][CH:27]([CH2:28][CH3:29])[CH2:30][CH3:31])[CH:7]=1)=[O:5])[CH3:2]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 44221278(3R,4S,5R)-4-(diethoxy-phosphorylamino)-3-(1-ethyl-propoxy)-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester

Product 1

HCID 57621534(3R,4S,5R)-4-amino-3-(1-ethyl-propoxy)-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl esterYield 64.8%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 120 mg of 18 and 500 μl EtOH in a 5 mL round-bottom flask equipped with a magnetic stirrer, a reflux condenser and an inert gas supply was added 120 μl sulphuric acid (96%). The reaction mixture was refluxed for 16 h, cooled to RT and diluted with 1.0 mL of EtOAc then cooled to 0-5° C. The cooled solution was treated with 100 μl of a 28% aqueous NaOH solution and with 257 μl of a 25% aqueous NH4OH. The well stirred mixture was diluted with 1.5 mL of water, extracted and the organic phase was separated, dried (Na2SO4), filtered and evaporated at 20° C./120-10 mbar and dried for 1 h at 20° C./<10 mbar to afford 56 mg of 20 as colorless oil.

Workup

  1. temperatureThe reaction mixture was refluxed for 16 h
  2. temperaturethen cooled to 0-5° C
  3. extractionextracted
  4. customthe organic phase was separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated at 20° C./120-10 mbar
  8. customdried for 1 h at 20° C./<10 mbar

Sources & evidence

ORD record
ord-6543f42eb85042f39cc1b770dec54557
Source dataset
uspto-grants-2009_05
Patent number
US07531687B2

Reaction notes

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