Tetrahydrofuran → HCID 86622975, compound

HRID 1712226Notes

Reaction equation

HRID 1712226 reaction equation
O1CCCC1.COC(C)(C)C.[CH:12]1([N:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][CH:28]3[C:29]([O:83][CH:84]([O:86][CH2:87][CH3:88])[CH3:85])([CH3:82])[CH2:30][CH2:31][CH:32]([O:74][Si](CC)(CC)CC)[CH2:33][C:34]([O:36][CH:37](/[C:42](/[CH3:73])=[CH:43]/[CH:44]=[CH:45]/[C:46]([CH3:72])([O:64][Si](CC)(CC)CC)[CH2:47][CH:48]4[O:63][CH:49]4[CH:50]([CH3:62])[CH:51]([O:54][Si](CC)(CC)CC)[CH2:52][CH3:53])[CH:38]([CH3:41])[CH:39]=[CH:40]3)=[O:35])=[O:26])[CH2:21][CH2:20]2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O>[CH:12]1([N:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][CH:28]3[C:29]([O:83][CH:84]([O:86][CH2:87][CH3:88])[CH3:85])([CH3:82])[CH2:30][CH2:31][CH:32]([OH:74])[CH2:33][C:34]([O:36][CH:37](/[C:42](/[CH3:73])=[CH:43]/[CH:44]=[CH:45]/[C:46]([OH:64])([CH3:72])[CH2:47][CH:48]4[O:63][CH:49]4[CH:50]([CH3:62])[CH:51]([OH:54])[CH2:52][CH3:53])[CH:38]([CH3:41])[CH:39]=[CH:40]3)=[O:35])=[O:26])[CH2:21][CH2:20]2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 15413tert-Butyl methyl etherHCID 2724141Tetrabutylammonium FluorideHCID 86622976HCID 86622976, compound

Product 1

HCID 86622975HCID 86622975, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under a nitrogen atmosphere and warming to hold the outside temperature at 25° C., tetrahydrofuran (145 mL) was added to a t-butyl methyl ether solution of the (8E,12E,14E)-7-{(4-cycloheptylpiperazin-1-yl)carbonyl}oxy-6-(1-ethoxyethoxy)-6,10,12,16,20-pentamethyl-3,16,21-tris(triethylsiloxy)-18,19-epoxytricosa-8,12,14-trien-11-olide obtained in Example 4, following which 93.8 mL (93.8 mmol) of a 1.0 M tetrahydrofuran solution of tetrabutylammonium fluoride was added dropwise over a period of 3 minutes. The reaction mixture was then stirred for 22 hours while being held at room temperature (25° C.). Water (145 mL) was added to this reaction mixture and the organic phase was separated, then washed with water (145 mL), yielding a t-butyl methyl ether/tetrahydrofuran solution of the title compound.

Workup

  1. temperatureUnder a nitrogen atmosphere and warming
  2. customat 25° C.
  3. additionwas added dropwise over a period of 3 minutes
  4. customwhile being held at room temperature
  5. custom(25° C.)
  6. customthe organic phase was separated
  7. washwashed with water (145 mL)

Sources & evidence

ORD record
ord-c1b1bce32ba049c1adac7f60e3ff09aa
Source dataset
uspto-grants-2010_09
Patent number
US07790887B2

Reaction notes

Loading…