Imidazole → HCID 131735290, compound

HRID 627217Notes

Reaction equation

HRID 627217 reaction equation
[CH2:1]([C:3](=[CH:15][CH3:16])[C@H:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:5][OH:6])[CH3:2].N1C=CN=C1.[CH3:22][C:23]([Si:26](Cl)([CH3:28])[CH3:27])([CH3:25])[CH3:24]>C(Cl)Cl.CN(C1C=CN=CC=1)C.C(OCC)C>[Si:26]([O:6][CH2:5][C@@H:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])/[C:3](/[CH2:1][CH3:2])=[CH:15]/[CH3:16])([C:23]([CH3:25])([CH3:24])[CH3:22])([CH3:28])[CH3:27]

Participants

7

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 89851813HCID 89851813, compound2×

Product 1

HCID 131735290HCID 131735290, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 3-ethyl-1-hydroxypent-3-en-2-ylcarbamate (Intermediate 202, 11.855 g, 51.70 mmol) in DCM (120 mL) was added imidazole (5.28 g, 77.55 mmol), DMAP (1.263 g, 10.34 mmol) and TBDMS-Cl (9.35 g, 62.04 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl ether and washed with brine. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. Purification by flash column chromatography (0-50% ethyl acetate/hexanes) afforded the title compound (17.20 g, 97%) as a clear oil.

Workup

  1. washwashed with brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash column chromatography (0-50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-8279092fd9324a75be15effeec585aea
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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