HCID 53338774, compound → HCID 86689964, compound

HRID 1427064Notes

Reaction equation

HRID 1427064 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([C@@H:13]1[CH2:26][CH2:25][C:16]2([O:20][C@H:19]([CH2:21][OH:22])[C@@H:18]([CH2:23][OH:24])[O:17]2)[CH:15]=[C:14]1[C:27]([O:29][CH2:30][CH3:31])=[O:28])(=[O:12])=[O:11].O.C(C(CCCC)C([O-])=O)C.[K+:43]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N-:9][S:10]([C@@H:13]1[CH2:26][CH2:25][C:16]2([O:17][C@H:18]([CH2:23][OH:24])[C@@H:19]([CH2:21][OH:22])[O:20]2)[CH:15]=[C:14]1[C:27]([O:29][CH2:30][CH3:31])=[O:28])(=[O:12])=[O:11].[K+:43]

Participants

4

Reactant 2

HCID 53338774HCID 53338774, compoundHCID 56947372HCID 56947372, compound

Product 1

HCID 86689964HCID 86689964, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

100 mg (0.208 mmol) of ethyl (2R,3R,8R)-8-[N-(2-chloro-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 162 in WO 2007/032362] was dissolved in 1 mL of ethyl acetate, and 2 mL of a solution containing 38 mg (0.208 mmol) of potassium 2-ethylhexanoate hydrate in ethyl acetate 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 92 mg of a crude product was obtained as an amorphous solid. Then, the crude product was dissolved in ethyl acetate, and the resulting solution was heated under reflux at 130° C. for 2 hours. After the resulting mixture was cooled, a precipitated solid was obtained by filtration and washed with ethyl acetate, whereby the title compound was obtained as a white crystal.

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

Sources & evidence

ORD record
ord-6a80adb1b47a4ef5a47d1d2fd478f3de
Source dataset
uspto-grants-2015_01
Patent number
US08933117B2

Reaction notes

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