tert-Butyl methyl ether → HCID 86622972, compound

HRID 1712224Notes

Reaction equation

HRID 1712224 reaction equation
NC(N)=N.[N+]([O-])(O)=O.NC(N)=N.C([O:16][CH:17]1[C:18]([O:72][CH:73]([O:75][CH2:76][CH3:77])[CH3:74])([CH3:71])[CH2:19][CH2:20][CH:21]([O:63][Si:64]([CH2:69][CH3:70])([CH2:67][CH3:68])[CH2:65][CH3:66])[CH2:22][C:23]([O:25][CH:26](/[C:31](/[CH3:62])=[CH:32]/[CH:33]=[CH:34]/[C:35]([CH3:61])([O:53][Si:54]([CH2:59][CH3:60])([CH2:57][CH3:58])[CH2:55][CH3:56])[CH2:36][CH:37]2[O:52][CH:38]2[CH:39]([CH3:51])[CH:40]([O:43][Si:44]([CH2:49][CH3:50])([CH2:47][CH3:48])[CH2:45][CH3:46])[CH2:41][CH3:42])[CH:27]([CH3:30])[CH:28]=[CH:29]1)=[O:24])(=O)C.COC(C)(C)C.[Cl-].[NH4+]>CO>[CH2:76]([O:75][CH:73]([O:72][C:18]1([CH3:71])[CH:17]([OH:16])[CH:29]=[CH:28][CH:27]([CH3:30])[CH:26](/[C:31](/[CH3:62])=[CH:32]/[CH:33]=[CH:34]/[C:35]([CH3:61])([O:53][Si:54]([CH2:59][CH3:60])([CH2:57][CH3:58])[CH2:55][CH3:56])[CH2:36][CH:37]2[O:52][CH:38]2[CH:39]([CH3:51])[CH:40]([O:43][Si:44]([CH2:45][CH3:46])([CH2:49][CH3:50])[CH2:47][CH3:48])[CH2:41][CH3:42])[O:25][C:23](=[O:24])[CH2:22][CH:21]([O:63][Si:64]([CH2:69][CH3:70])([CH2:67][CH3:68])[CH2:65][CH3:66])[CH2:20][CH2:19]1)[CH3:74])[CH3:77]

Participants

6

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 25517Ammonium ChlorideHCID 86601416HCID 86601416, compoundHCID 86622973HCID 86622973, compound

Product 1

HCID 86622972HCID 86622972, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
24.700000762939453 °C

Procedure

Under a nitrogen atmosphere and warming to hold the outside temperature at 25° C., 104 mL (20.8 mmol) of a 0.2 M solution of guanidine/guanidine nitrate in methanol was added to a methanol (79 mL) solution containing 18.4 g of (8E,12E,14E)-7-acetoxy-6-(1-ethoxyethoxy)-6,10,12,16,20-pentamethyl-3,16,21-tris(triethylsiloxy)-18,19-epoxytricosa-8,12,14-trien-11-olide, following which stirring was carried out for 6 hours with maintaining the internal temperature at from 24.9 to 24.5° C. The reaction mixture was then ice-cooled and 276 mL of t-butyl methyl ether was added, following which 184 mL of a 10% aqueous solution of ammonium chloride was added. The organic phase was then separated, washed successively with water (184 mL) and a 4% saline solution (184 mL), and subsequently dried over magnesium sulfate (18.4 g). After drying, the magnesium sulfate was removed by filtration, following which the filtrate was washed with t-butyl methyl ether (55 mL) then evaporated at 40° C., yielding 19.7 g of a crude form (yellow oily substance) of the title compound (content: 73.4%; by weight, 14.5 g).

Workup

  1. temperatureUnder a nitrogen atmosphere and warming
  2. customat 25° C.
  3. temperatureice-cooled
  4. additionwas added
  5. customThe organic phase was then separated
  6. washwashed successively with water (184 mL)
  7. dry with materiala 4% saline solution (184 mL), and subsequently dried over magnesium sulfate (18.4 g)
  8. customAfter drying
  9. customthe magnesium sulfate was removed by filtration
  10. washwas washed with t-butyl methyl ether (55 mL)
  11. customthen evaporated at 40° C.

Sources & evidence

ORD record
ord-006cd1ff78db46698d4205348ef65d5d
Source dataset
uspto-grants-2010_09
Patent number
US07790887B2

Reaction notes

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