Sodium Sulfite → HCID 57771526, compound

HRID 2070593Notes

Reaction equation

HRID 2070593 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][C@@H:5]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH2:27][CH2:26][CH2:25][C@@:19]3([CH2:23][C@H:22]([OH:24])[CH2:21][CH2:20]3)[CH:18]=2)=[CH:11][CH:10]=1)[C:6]#[C:7][CH3:8].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:28])[CH2:4][C@@H:5]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH2:27][CH2:26][CH2:25][C@@:19]3([CH2:23][C:22](=[O:24])[CH2:21][CH2:20]3)[CH:18]=2)=[CH:11][CH:10]=1)[C:6]#[C:7][CH3:8]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 159087TriacetoxyperiodinaneHCID 57771364HCID 57771364, compound

Product 1

HCID 57771526HCID 57771526, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of (3S)-3-[4-((2R,5R)-2-hydroxy-spiro[4.5]dec-6-en-7-ylmethoxy)-phenyl]-hex-4-ynoic acid methyl ester (195 mg) obtained in Step 9 of Example 104 in chloroform (2 mL) was added 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (Dess-Martin periodinane; 259 mg) under ice-cooling, followed by stirring the mixture under ice-cooling for 3 hours and then at room temperature for 1 hour. To the reaction mixture was added aqueous sodium sulfite solution, followed by extraction with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium bicarbonate solution and saturated brine, dried and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:6 to 1:4) to give (3S)-3-[4-((5R)-2-oxo-spiro[4.5]dec-6-en-7-ylmethoxy)-phenyl]-hex-4-ynoic acid methyl ester (190 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling for 3 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed successively with saturated aqueous sodium bicarbonate solution and saturated brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:6 to 1:4)

Sources & evidence

ORD record
ord-5258285dcf6d4eb288261cc60bc46d4b
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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