Potassium Hydroxide → HCID 86678283, compound

HRID 2407886Notes

Reaction equation

HRID 2407886 reaction equation
[OH:1][CH2:2][C@@H:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4].[OH-].[K+].Br[CH2:16][CH2:17][CH2:18][P:19](=[O:26])([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22]>C1COCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:24]([O:23][P:19]([CH2:18][CH2:17][CH2:16][O:1][CH2:2][C@@H:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4])([O:20][CH2:21][CH3:22])=[O:26])[CH3:25]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 283500Diethyl (3-bromopropyl)phosphonateHCID 70231031,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamate

Product 1

HCID 86678283HCID 86678283, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-tert-butyl 1-hydroxypropan-2-ylcarbamate (1 eq, from the previous step) in THF (0.1 M) at room temperature was added KOH (5 eq), tetrabutylammonium bromide (0.1 eq), and diethyl 3-bromopropylphosphonate (2 eq). The reaction was stirred at room temperature overnight. The mixture was concentrated en vaccuo and then taken up in DCM/water. The aqueous layer was extracted with DCM (2×). The combined organic layers were dried over anhydrous MgSO4, and concentrated en vaccuo. The crude mixture was purified by flash chromatography on a COMBIFLASH® system (ISCO) using a gradient of 0-100% ethyl acetate in hexanes and then 100% ethyl acetate to give the product as an oil.

Workup

  1. concentrationThe mixture was concentrated en vaccuo
  2. extractionThe aqueous layer was extracted with DCM (2×)
  3. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  4. concentrationconcentrated en vaccuo
  5. customThe crude mixture was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-f7310bc8edfc40d097fdef9f5424356f
Source dataset
uspto-grants-2014_08
Patent number
US08808703B2

Reaction notes

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