Diisopropylethylamine → HCID 86681466, compound

HRID 339974Notes

Reaction equation

HRID 339974 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=O)=[C:4]([CH2:12]Br)[CH:3]=1.[NH2:14][C@@H:15]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:16]O.C([N:28](CC)C(C)C)(C)C>C(O)CCC>[NH2:28][CH2:16][C@@H:15]([N:14]1[CH2:12][C:4]2[C:5](=[CH:10][CH:11]=[C:2]([Br:1])[CH:3]=2)[C:6]1=[O:8])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 447213phenylalaninol, (S)-HCID 22031079Methyl 4-bromo-2-(bromomethyl)benzoate

Product 1

HCID 86681466HCID 86681466, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of methyl 4-bromo-2-(bromomethyl)benzoate (1.0 g, 3.24 mmol), (2S)-2-amino-3-phenyl-1-propanol (0.49 g, 3.24 mmol) and N,N-diisopropylethylamine (2.06 mL, 11.8 mmol) in 1-butanol (8 mL) was stirred at 140° C. for 2 h under microwave. After the reaction mixture was concentrated under reduced pressure, the residue was dissolved in water (20 mL) and EtOAc (20 mL). The organic phase was separated and the aqueous layer was extracted with EtOAc (2×30 mL). The combined organic phases were washed with water, brine and dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by combi-flash chromatography eluted with MeOH/EtOAc (0-5%) to give 0.8 g (71% yield) of the final product as off-white solid. LC/MS found: 346.0 (M+H)+.

Workup

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in water (20 mL)
  3. customThe organic phase was separated
  4. extractionthe aqueous layer was extracted with EtOAc (2×30 mL)
  5. washThe combined organic phases were washed with water, brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by combi-flash chromatography
  10. washeluted with MeOH/EtOAc (0-5%)

Sources & evidence

ORD record
ord-328ed6f253294ab7960c0d5afc6c09a9
Source dataset
uspto-grants-2014_11
Patent number
US08895571B2

Reaction notes

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