Water → HCID 178444561, compound

HRID 500082Notes

Reaction equation

HRID 500082 reaction equation
[CH2:1](S(C1N(C2C=CC=CC=2)N=NN=1)(=O)=O)[CH3:2].C[Si](C)(C)N[Si](C)(C)C.[K].[CH:27]([CH2:29][CH2:30][C@H:31]1[CH2:36][CH2:35][C@H:34]([NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH2:33][CH2:32]1)=O.O>COCCOC>[CH2:30]([C@H:31]1[CH2:36][CH2:35][C@H:34]([NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH2:33][CH2:32]1)[CH2:29]/[CH:27]=[CH:1]/[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 7536625-Ethylsulfonyl-1-phenyl-1H-tetrazoleHCID 45051783Silanamine, 1,1,1-trimethyl-N-(trimethylsilyl)-, potassium saltHCID 178453885HCID 178453885, compound

Product 1

HCID 178444561HCID 178444561, compoundYield 9.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

To a mixture of 5-ethylsulfonyl-1-phenyl-1H-tetrazole (5.0 g) and anhydrous ethylene glycol dimethyl ether (50 ml) at −60° C. was added 0.5 M potassium hexamethyldisilazane solution (in toluene, 19.7 ml), and the mixture was stirred for 20 minutes. Under the same condition, a solution of t-butyl trans-4-(2-formylethyl)cyclohexylcarbamate (2.65 g) (Example 73 (3)) in anhydrous ethylene glycol dimethyl ether (20 ml) was added thereto. The reaction mixture was gradually warmed to 25° C. and stirred overnight. To the reaction mixture was added water, and the mixture was stirred for 1 hour, then extracted with diethyl ether. The organic layer was washed with brine, dried over sodium sulfate, and then the solvent was removed in vacuo. The residue was purified by a silica gel chromatography (eluent: gradient from 100% hexane/0% ethyl acetate to 0% hexane/100% ethyl acetate) to give 252 mg of t-butyl trans-4-[(E)-3-pentenyl]cyclohexylcarbamate.

Workup

  1. stirringstirred overnight
  2. stirringthe mixture was stirred for 1 hour
  3. extractionextracted with diethyl ether
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was removed in vacuo
  7. customThe residue was purified by a silica gel chromatography (eluent: gradient from 100% hexane/0% ethyl acetate to 0% hexane/100% ethyl acetate)

Sources & evidence

ORD record
ord-bab4c500ebb74311b1bd2fc309cf5833
Source dataset
uspto-grants-2010_08
Patent number
US07767854B2

Reaction notes

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