p-Toluenesulfonic acid → HCID 68794057, compound

HRID 1713603Notes

Reaction equation

HRID 1713603 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][C@:10]21[C:48]1[C:43](=[CH:44][C:45]([Cl:58])=[C:46]([CH2:49][C:50]3[CH:55]=[CH:54][C:53]([CH2:56][CH3:57])=[CH:52][CH:51]=3)[CH:47]=1)[O:42][CH:41]([OH:59])[CH2:40]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:60]1(C)C=CC(S(O)(=O)=O)=CC=1>CO.COC(OC)OC>[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][C@:10]21[C:48]1[C:43](=[CH:44][C:45]([Cl:58])=[C:46]([CH2:49][C:50]3[CH:55]=[CH:54][C:53]([CH2:56][CH3:57])=[CH:52][CH:51]=3)[CH:47]=1)[O:42][CH:41]([O:59][CH3:60])[CH2:40]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 68795104HCID 68795104, compound

Product 1

HCID 68794057HCID 68794057, compoundYield 104.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 9005Trimethyl orthoformateSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 41 (85 mg, 105 μmol) in anhydrous MeOH (1 mL) and trimethylorthoformate (0.5 mL) was added 4-toluenesulfonic acid (15 mg). The mixture was heated in a closed vial at 65° C. for 2 h, cooled to rt, evaporated, loaded onto a preparatory TLC plate, and developed using 15% EtOAc in petroleum ether to yield 42 (75 mg, 91% yield) as two diastereomers. LCMS m/z 847 (M+Na).

Workup

  1. temperaturecooled to rt
  2. customevaporated

Sources & evidence

ORD record
ord-94029bffd733418cadee4a9cdef5f518
Source dataset
uspto-grants-2010_09
Patent number
US07795228B2

Reaction notes

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