HCID 53338774, compound → HCID 86689965, compound

HRID 1427065Notes

Reaction equation

HRID 1427065 reaction equation
O.C(C(CCCC)C([O-])=O)C.[K+:12].[Br:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[NH:21][S:22]([C@@H:25]1[CH2:38][CH2:37][C:28]2([O:32][C@H:31]([CH2:33][OH:34])[C@@H:30]([CH2:35][OH:36])[O:29]2)[CH:27]=[C:26]1[C:39]([O:41][CH2:42][CH3:43])=[O:40])(=[O:24])=[O:23]>C(OCC)(=O)C>[Br:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[N-:21][S:22]([C@@H:25]1[CH2:38][CH2:37][C:28]2([O:29][C@H:30]([CH2:35][OH:36])[C@@H:31]([CH2:33][OH:34])[O:32]2)[CH:27]=[C:26]1[C:39]([O:41][CH2:42][CH3:43])=[O:40])(=[O:24])=[O:23].[K+:12]

Participants

4

Reactant 2

HCID 53338774HCID 53338774, compoundHCID 56947370HCID 56947370, compound

Product 1

HCID 86689965HCID 86689965, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

422 mg (2.31 mmol) of potassium 2-ethylhexanoate hydrate was dissolved in 23 mL of ethyl acetate, and 1.215 g (2.31 mmol) of ethyl(2R,3R,8R)-8-[N-(2-bromo-4-fluorophenyl)sulfamoyl]-2,3-bis(hydroxymethyl)-1,4-dioxaspiro[4.5]deca-6-ene-7-carboxylate [a compound described as a low polarity compound (first peak) of Example 166 in WO 2007/032362] was added thereto under stirring at room temperature. The resulting reaction solution was concentrated under reduced pressure, and to the residue, diethyl ether was added. A precipitated solid was obtained by filtration and washed with diethyl ether, whereby 954 mg of a crude product was obtained as an amorphous solid. Then, the crude product was dissolved in 6 mL of ethyl acetate, and the resulting solution was heated under stirring at 70° C. for 5 minutes. After the resulting mixture was cooled, a precipitated solid was obtained by filtration and washed with ethyl acetate and diethyl ether, whereby 850 mg of the title compound was obtained as a white crystal (yield: 65%).

Workup

  1. additionwas added
  2. customThe resulting reaction solution
  3. concentrationwas concentrated under reduced pressure
  4. additionto the residue, diethyl ether was added
  5. customA precipitated solid was obtained by filtration
  6. washwashed with diethyl ether
  7. customwhereby 954 mg of a crude product was obtained as an amorphous solid
  8. temperaturethe resulting solution was heated
  9. stirringunder stirring at 70° C. for 5 minutes
  10. temperatureAfter the resulting mixture was cooled
  11. customa precipitated solid was obtained by filtration
  12. washwashed with ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-db1f873ad9154578b1d72b05ae779c55
Source dataset
uspto-grants-2015_01
Patent number
US08933117B2

Reaction notes

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