Cesium carbonate → HCID 178499983, compound

HRID 516898Notes

Reaction equation

HRID 516898 reaction equation
[Si:1]([O:8][C@@H:9]1[CH2:14][CH2:13][C@H:12](/[C:15](=[C:20](\[CH2:25][C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)/[C:21]([O:23][CH3:24])=[O:22])/[C:16]([O:18][CH3:19])=[O:17])[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:40][CH2:41][NH:42][C:43](=[O:49])[O:44][C:45]([CH3:48])([CH3:47])[CH3:46]>CN(C=O)C.O>[C:45]([O:44][C:43]([NH:42][CH2:41][CH2:40][O:32][C:29]1[CH:28]=[CH:27][C:26]([CH2:25]/[C:20](=[C:15](\[C@H:12]2[CH2:13][CH2:14][C@@H:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:10][CH2:11]2)/[C:16]([O:18][CH3:19])=[O:17])/[C:21]([O:23][CH3:24])=[O:22])=[CH:31][CH:30]=1)=[O:49])([CH3:48])([CH3:47])[CH3:46]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 178499946HCID 178499946, compound

Product 1

HCID 178499983HCID 178499983, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of dimethyl 2-(cis-4-((tert-butyldimethylsilyl)oxy)cyclohexyl)-3-(4-hydroxybenzyl)maleate (35 mg, 0.075 mmol) and cesium carbonate (27 mg, 0.083 mmol) in DMF (1.2 ml) was cooled to 0° C., a solution of tert-butyl (2-bromoethyl)carbamate (20 mg, 0.091 mmol) in DMF (0.5 ml) was added dropwise, and the mixture was stirred at room temperature for 19 hr. The reaction mixture was diluted with water and was extracted with ethyl acetate, the organic layer was washed with saturated brine and was dried over anhydrous sodium sulfate, and the filtrate was removed by distillation under reduced pressure. The residue was chromatographed on silica gel column (hexane:ethyl acetate=8:2) to give the title compound as an oil (20 mg, yield 43%).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washthe organic layer was washed with saturated brine
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. customthe filtrate was removed by distillation under reduced pressure
  5. customThe residue was chromatographed on silica gel column (hexane:ethyl acetate=8:2)

Sources & evidence

ORD record
ord-25057840044d4fe8869a6c986783344e
Source dataset
uspto-grants-2015_08
Patent number
US09115079B2

Reaction notes

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