Acetic Anhydride → (3R,4S,5R)-4-acetylamino-3-(1-ethyl-propoxy)-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester

HRID 492259Notes

Reaction equation

HRID 492259 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]([NH2:17])[C@H:8]([O:18][CH:19]([CH2:22][CH3:23])[CH2:20][CH3:21])[CH:7]=1)=[O:5])[CH3:2].C(=O)([O-])O.[Na+].[C:29](OC(=O)C)(=[O:31])[CH3:30]>CCOC(C)=O>[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]([NH:17][C:29](=[O:31])[CH3:30])[C@H:8]([O:18][CH:19]([CH2:20][CH3:21])[CH2:22][CH3:23])[CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 57621534(3R,4S,5R)-4-amino-3-(1-ethyl-propoxy)-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester

Product 1

HCID 42599441(3R,4S,5R)-4-acetylamino-3-(1-ethyl-propoxy)-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 190 mg of 20 and EtOAc (1.6 mL) in a 10 mL round-bottom flask equipped with a magnetic stirrer and an inert gas supply was added was added at RT aqueous 1 M sodium hydrogen carbonate (1.6 mL). To the resulting mixture was added 62 μl of acetic anhydride and the 2-phase mixture was stirred for 1 h at RT. The mixture was diluted with 2.0 mL of EtOAc, the organic phase was separated, dried (Na2SO4), filtered and the filter cake was washed with total 3.0 mL EtOAc. The filtrate was evaporated at 40° C./200-10 mbar to afford 192 mg of 22 as off white crystals.

Workup

  1. additionan inert gas supply was added
  2. customthe organic phase was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. washthe filter cake was washed with total 3.0 mL EtOAc
  6. customThe filtrate was evaporated at 40° C./200-10 mbar

Sources & evidence

ORD record
ord-fcb4866cc960442a92e1df0d7abb9b1c
Source dataset
uspto-grants-2009_05
Patent number
US07531687B2

Reaction notes

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