HCID 69055140, compound → HCID 69060779, compound

HRID 1727226Notes

Reaction equation

HRID 1727226 reaction equation
[C:1]([O:4][C@H:5]1[C@@H:14]2[O:15]C(C)(C)[O:17][C@@:13]32[C@H:8]([C@H:9]([C:21]2[N:22]=[C:23]([CH2:26][CH3:27])[S:24][CH:25]=2)[CH2:10][CH2:11][C@H:12]3[CH3:20])[CH:7]=[C:6]1[CH3:28])(=[O:3])[CH3:2]>C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:1]([O:4][C@@H:5]1[C:6]([CH3:28])=[CH:7][C@@H:8]2[C@:13]([OH:17])([C@H:12]([CH3:20])[CH2:11][CH2:10][C@H:9]2[C:21]2[N:22]=[C:23]([CH2:26][CH3:27])[S:24][CH:25]=2)[C@H:14]1[OH:15])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 69055140HCID 69055140, compound

Product 1

HCID 69060779HCID 69060779, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidSolvent

Procedure

A solution of (3aS,4R,6aS,7R,10R,10aR)-7-(2-ethyl-1,3-thiazol-4-yl)-2,2,5,10-tetramethyl-4,6a,7,8,9,10-hexahydro-3aH-naphtho[1,8a-d][1,3]dioxol-4-yl acetate (Preparation 165, 345 mg) in methanolic para-toluenesulfonic acid (1% w/w, 10 ml) was stirred at room temperature for 12 days. The reaction mixture was partitioned between ethyl acetate and a mixture of dilute aqueous sodium chloride and saturated aqueous sodium hydrogen carbonate. The organic phase was dried (MgSO4), evaporated and purified by flash column chromatography on silica gel using a gradient elution ethyl acetate:hexane (1:5 to 1:1) to give the product as a gum (94 mg).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate
  2. additiona mixture of dilute aqueous sodium chloride and saturated aqueous sodium hydrogen carbonate
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customevaporated
  5. custompurified by flash column chromatography on silica gel using
  6. washa gradient elution ethyl acetate:hexane (1:5 to 1:1)

Sources & evidence

ORD record
ord-8143bd3d668a4404a2eba4b80d2c51d5
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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