tert-Butanol → HCID 57723592, compound

HRID 1436974Notes

Reaction equation

HRID 1436974 reaction equation
[CH2:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH:13]2[C:14]([O:47]C(OCC)C)([CH3:46])[CH2:15][CH2:16][CH:17]([OH:45])[CH2:18][C:19]([O:21][CH:22](/[C:27](/[CH3:44])=[CH:28]/[CH:29]=[CH:30]/[C:31]([OH:43])([CH3:42])[CH2:32][CH:33]3[O:41][CH:34]3[CH:35]([CH3:40])[CH:36]([OH:39])[CH2:37][CH3:38])[CH:23]([CH3:26])[CH:24]=[CH:25]2)=[O:20])=[O:11])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.CC(O)(C)C>O1CCCC1>[CH2:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]([O:12][CH:13]2[C:14]([OH:47])([CH3:46])[CH2:15][CH2:16][CH:17]([OH:45])[CH2:18][C:19]([O:21][CH:22](/[C:27](/[CH3:44])=[CH:28]/[CH:29]=[CH:30]/[C:31]([OH:43])([CH3:42])[CH2:32][CH:33]3[O:41][CH:34]3[CH:35]([CH3:40])[CH:36]([OH:39])[CH2:37][CH3:38])[CH:23]([CH3:26])[CH:24]=[CH:25]2)=[O:20])=[O:11])[CH2:8][CH2:9]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86602613HCID 86602613, compound2×

Product 1

HCID 57723592HCID 57723592, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To Compound 46 (8E,12E,14E)-7-((4-allylpiperazin-1-yl)carbonyl)oxy-6-(1-ethoxyethoxy)-3,16,21-trihydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (8.7 mg, 12 μmol) obtained in Example 46 was added a solution of pyridinium p-toluenesulfonate (3.3 mg, 13 μmol) in a mixture of tetrahydrofuran:2-methyl-2-propanol=1:1 (1 mL) at room temperature, and the reaction mixture was stirred at the same temperature for 17 hours. The reaction mixture was concentrated. The resulting residue was purified by thin layer chromatography (Fuji Silysia, NH Silica gel Plate; methanol:dichloromethane=5:95) to give the title compound (5.5 mg, 70%) as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe resulting residue was purified by thin layer chromatography (Fuji Silysia, NH Silica gel Plate; methanol:dichloromethane=5:95)

Sources & evidence

ORD record
ord-7002168195ac4b2598666f9ed4a0a4cc
Source dataset
uspto-grants-2009_11
Patent number
US07619100B2

Reaction notes

Loading…