Sulfuric Acid → HCID 86641126, compound

HRID 2191046Notes

Reaction equation

HRID 2191046 reaction equation
[C:1]([O:9][C@@H:10]1[C@H:14]([F:15])[C@@H:13]([CH2:16][CH:17]([P:25]([O:30][CH2:31][CH3:32])([O:27][CH2:28][CH3:29])=[O:26])[S:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)O[C@@H]1OC)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[C:40]([O-:43])([OH:42])=O.[Na+].[C:45](OC(=O)C)(=[O:47])[CH3:46]>C(O)(=O)C>[C:1]([O:9][C@@H:10]1[C@H:14]([F:15])[C@@H:13]([CH2:16][CH:17]([P:25]([O:30][CH2:31][CH3:32])([O:27][CH2:28][CH3:29])=[O:26])[S:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[O:42][C@H:40]1[O:43][C:45](=[O:47])[CH3:46])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 59289351HCID 59289351, compound

Product 1

HCID 86641126HCID 86641126, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Compound 35.13 (50 mg, 0.1 mmol) was dissolved in a 10% solution of acetic anhydride in acetic acid (2.2 mL). Concentrated sulfuric acid was added and the mixture was stirred at r.t. for 2 h. The mixture was then poured into a 5% aqueous solution of NaHCO3 (100 mL) containing 50 g of ice. The aqueous phase was then extracted with 2×100 mL CH2Cl2. The extracts were combined, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography to give compound 35.14 (60 mg, 95% yield).

Workup

  1. extractionThe aqueous phase was then extracted with 2×100 mL CH2Cl2
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d371fb5ab08f49e48c234cd854faf3da
Source dataset
uspto-grants-2012_12
Patent number
US08324179B2

Reaction notes

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