Potassium Hydroxide → HCID 86678286, compound

HRID 2407891Notes

Reaction equation

HRID 2407891 reaction equation
[OH:1][CH2:2][C:3]1([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:5][CH2:4]1.[OH-].[K+].Br[CH2:17][CH2:18][CH2:19][P:20](=[O:27])([O:24][CH2:25][CH3:26])[O:21][CH2:22][CH3:23]>C1COCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:25]([O:24][P:20]([CH2:19][CH2:18][CH2:17][O:1][CH2:2][C:3]1([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11])[CH2:4][CH2:5]1)([O:21][CH2:22][CH3:23])=[O:27])[CH3:26]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 283500Diethyl (3-bromopropyl)phosphonateHCID 11286907tert-butyl N-(1-(hydroxymethyl)cyclopropyl)carbamate

Product 1

HCID 86678286HCID 86678286, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 1-(hydroxymethyl)cyclopropylcarbamate (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-6828d81a4b9b4ddd9f37377607bb0e6b
Source dataset
uspto-grants-2014_08
Patent number
US08808703B2

Reaction notes

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