tert-Butanol → HCID 57723592, compound

HRID 1366329Notes

Reaction equation

HRID 1366329 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-f0357047439d4e5990479a3a934081ec
Source dataset
uspto-grants-2011_02
Patent number
US07893068B2

Reaction notes

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