Allyl bromide → HCID 45789233, compound

HRID 1432099Notes

Reaction equation

HRID 1432099 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:19](Br)[CH:20]=[CH2:21]>CN(C=O)C.C1COCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH2:21]([N:11]([C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH:20]=[CH2:19]

Participants

7

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 75313N-Benzyloxycarbonyl-beta-alanine

Product 1

HCID 45789233HCID 45789233, compound

Reagents, catalysts & solvents 3

HCID 311Citric AcidSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2.5 g (11.2 mmol) 3-benzyloxycarbonylamino-propionic acid in 30 ml DMF and 30 ml THF are added 1.34 g (33.6 mmol, 60% suspension in mineral oil) NaH and the mixture is heated at 60° C. for 3 h. After cooling down 1.42 ml (16.8 mmol) allyl bromide are added. After stirring for 40 h at rt the mixture is diluted with 10% citric acid and extracted three times with EtOAc. The combined organic layers are washed with water, dried with sodium sulfate and the volatiles are removed in vacuo. The residue is chromatographed on silica gel (hexane/EtOAc 3:1), yielding the title product.

Workup

  1. additionare added
  2. extractionextracted three times with EtOAc
  3. washThe combined organic layers are washed with water
  4. dry with materialdried with sodium sulfate
  5. customthe volatiles are removed in vacuo
  6. customThe residue is chromatographed on silica gel (hexane/EtOAc 3:1)

Sources & evidence

ORD record
ord-18c9094c289241259ad93c06327e300a
Source dataset
uspto-grants-2009_11
Patent number
US07612055B2

Reaction notes

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