p-Toluenesulfonic acid → HCID 86650573, compound

HRID 1971741Notes

Reaction equation

HRID 1971741 reaction equation
[CH2:1]([O:3][C:4](=[O:37])[C@H:5]([OH:36])[C@H:6]([C:8]1[C:9]([O:34][CH3:35])=[CH:10][C:11]2[CH2:12][CH2:13][N:14]3[C:20]4[C:21](=[O:33])[N:22]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:23][CH2:24][C:25]([CH3:28])([CH3:27])[CH2:26][C:19]=4[CH:18]=[C:15]3[C:16]=2[CH:17]=1)[OH:7])[CH3:2].[C:38]1(C)[CH:43]=CC(S(O)(=O)=O)=C[CH:39]=1.C(N(CC)CC)C>CC(C)=O.COC(OC)(C)C>[C:29]([N:22]1[CH2:23][CH2:24][C:25]([CH3:27])([CH3:28])[CH2:26][C:19]2[CH:18]=[C:15]3[C:16]4[CH:17]=[C:8]([C@@H:6]5[O:7][C:38]([CH3:43])([CH3:39])[O:36][C@H:5]5[C:4]([O:3][CH2:1][CH3:2])=[O:37])[C:9]([O:34][CH3:35])=[CH:10][C:11]=4[CH2:12][CH2:13][N:14]3[C:20]=2[C:21]1=[O:33])([CH3:30])([CH3:31])[CH3:32]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 66919936HCID 66919936, compound

Product 1

HCID 86650573HCID 86650573, compoundYield 1,722.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 64952,2-DimethoxypropaneSolvent

Procedure

A solution of 868 mg of 21c in 10 ml of acetone, 2.2 ml of 2,2-dimethoxypropane, and 17 mg of p-toluenesulfonic acid was stirred for 2 hr. The reaction was treated with 0.8 ml of triethylamine, stirred for 5 min, and then concentrated to a small volume and diluted with 30 ml of 5% NaHCO3 solution. The product was extracted with ethyl acetate and the extracts were washed with water, dried and concentrated, to provide 940 mg of product 21d, which was used as is in the next step; Rf (heptane/ethyl acetate 1/1) 0.57.

Workup

  1. concentrationconcentrated to a small volume
  2. additiondiluted with 30 ml of 5% NaHCO3 solution
  3. extractionThe product was extracted with ethyl acetate
  4. washthe extracts were washed with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-77a91e1721f34b3d86fb74110f27b59b
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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