p-Toluenesulfonic acid → HCID 86593736, compound

HRID 272102Notes

Reaction equation

HRID 272102 reaction equation
[CH2:1]([O:8][CH:9]1[CH:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:12]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:11]([OH:39])[C:10]1([OH:43])[CH2:40][CH2:41][CH3:42])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[C:46](OC)([CH3:48])[CH3:47].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>CC(C)=O>[CH2:1]([O:8][CH:9]1[C:10]2([CH2:40][CH2:41][CH3:42])[CH:11]([O:39][C:46]([CH3:48])([CH3:47])[O:43]2)[CH:12]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:13]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:14]1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 8471TriethylamineHCID 86593734HCID 86593734, compound

Product 1

HCID 86593736HCID 86593736, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

21 (0.22 g, 0.37 mmol) was dissolved in 20 mL dry acetone. 5 mL (40.8 mmol) 2.2-dimethoxypropane and 48 mg (0.25 mmol) p-toluene sulfonic acid were added an the solution was stirred for three days at room temperature. Then the reaction was stopped by adding 150 μL (1.08 mmole) triethylamine. All volatile components were removed under reduced pressure and the residue was dissolved in t-butylmethyl ether and washed with 0.5 M phosphate buffer pH=7 and brine. The organic phase was dried over Na2SO4, filtered and dried under reduced pressure. The residue was purified by preparative HPLC (RP18, 94% MeOH, 40 mL/min, tRet=35.10 min) to give 22 (160 mg, 0.25 mmol, 69.3% yield) as a slightly yellow oil.

Workup

  1. customAll volatile components were removed under reduced pressure
  2. dissolutionthe residue was dissolved in t-butylmethyl ether
  3. washwashed with 0.5 M phosphate buffer pH=7 and brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. customdried under reduced pressure
  7. customThe residue was purified by preparative HPLC (RP18, 94% MeOH, 40 mL/min, tRet=35.10 min)

Sources & evidence

ORD record
ord-cdad1390d73245e9b9a13185bc8ecd89
Source dataset
uspto-grants-2008_11
Patent number
US07453006B2

Reaction notes

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