Tetrahydrofuran → HCID 11765422, compound

HRID 1712227Notes

Reaction equation

HRID 1712227 reaction equation
O1CCCC1.[CH:6]1([N:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][CH:22]3[C:23]([O:56]C(OCC)C)([CH3:55])[CH2:24][CH2:25][CH:26]([OH:54])[CH2:27][C:28]([O:30][CH:31](/[C:36](/[CH3:53])=[CH:37]/[CH:38]=[CH:39]/[C:40]([OH:52])([CH3:51])[CH2:41][CH:42]4[O:50][CH:43]4[CH:44]([CH3:49])[CH:45]([OH:48])[CH2:46][CH3:47])[CH:32]([CH3:35])[CH:33]=[CH:34]3)=[O:29])=[O:20])[CH2:15][CH2:14]2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(=O)(O)[O-].[Na+]>COC(C)(C)C.COC(C)(C)C.O1CCCC1.C(O)(C)(C)C>[CH:6]1([N:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][CH:22]3[C:23]([OH:56])([CH3:55])[CH2:24][CH2:25][CH:26]([OH:54])[CH2:27][C:28]([O:30][CH:31](/[C:36](/[CH3:53])=[CH:37]/[CH:38]=[CH:39]/[C:40]([OH:52])([CH3:51])[CH2:41][CH:42]4[O:50][CH:43]4[CH:44]([CH3:49])[CH:45]([OH:48])[CH2:46][CH3:47])[CH:32]([CH3:35])[CH:33]=[CH:34]3)=[O:29])=[O:20])[CH2:15][CH2:14]2)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 86622975HCID 86622975, compound

Product 1

HCID 11765422HCID 11765422, compound

Reagents, catalysts & solvents 3

HCID 6386tert-ButanolSolventHCID 15413tert-Butyl methyl etherSolventHCID 22492792Mtbe thfSolvent

Procedure

At an outside temperature of 25° C., tetrahydrofuran (145 mL) and t-butanol (62.1 mL) were added to a t-butyl methyl ether/tetrahydrofuran solution of the (8E,12E,14E)-7-{(4-cycloheptylpiperazin-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 obtained in Example 5, following which 11.8 g (46.9 mmol) of pyridinium p-toluenesulfonate was added and stirring was carried out for 3 hours. Next, t-butyl methyl ether (104 mL) and a saturated aqueous solution of sodium bicarbonate (104 mL) were added to the reaction mixture, following which the organic phase was separated and washed with a 4% saline solution (104 mL), then evaporated, yielding 50.6 g (content: 20.2%; by weight, 10.2 g) of a crude form (yellow oily substance) of the title compound.

Workup

  1. additionwas added
  2. customwas separated
  3. washwashed with a 4% saline solution (104 mL)
  4. customevaporated

Sources & evidence

ORD record
ord-d7b04f70e0d24100abbd0b8f572338e4
Source dataset
uspto-grants-2010_09
Patent number
US07790887B2

Reaction notes

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