Benzyl Bromide → HCID 14557752, compound

HRID 1507921Notes

Reaction equation

HRID 1507921 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl.[NH2:16][C@H:17]([CH3:22])[C:18]([O:20][CH3:21])=[O:19]>C(#N)C>[CH3:21][O:20][C:18](=[O:19])[C@H:17]([N:16]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:22]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 11182647Methyl D-alaninate hydrochloride

Product 1

HCID 14557752HCID 14557752, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Potassium carbonate (49.5 g, 358 mmol) and benzyl bromide (42.5 mL, 358 mmol) were each added to a partial solution of (R)-methyl 2-aminopropanoate hydrochloride (10 g, 71.6 mmol) in acetonitrile (200 mL) and the reaction was allowed to stir at 60° C. overnight. The reaction was filtered and the filtrate evaporated in vacuo. The residue was purified by column chromatography using hexane (to elute the excess benzyl bromide) followed by 5:1 hexane:ethyl acetate to elute the product. After concentration and drying of the fractions containing the major product, the title compound (20.13 g, 71.0 mmol, 99% yield) was obtained as a colorless oil. HPLC (condition B): retention time=2.80 min. LCMS (condition B): m/z 284.2. 1H NMR (500 MHz, MeOD) δ ppm 7.38-7.44 (4 H, m), 7.34 (4 H, t, J=7.63 Hz), 7.22-7.30 (2 H, m), 3.84 (2 H, d, J=13.87 Hz), 3.77 (3 H, s), 3.65 (2 H, d, J=13.87 Hz), 3.52 (1 H, q, J=7.12 Hz), 1.35 (3 H, d, J=7.21 Hz).

Workup

  1. filtrationThe reaction was filtered
  2. customthe filtrate evaporated in vacuo
  3. customThe residue was purified by column chromatography
  4. washto elute the excess benzyl bromide)
  5. washethyl acetate to elute the product
  6. concentrationAfter concentration
  7. customdrying of the fractions
  8. additioncontaining the major product

Sources & evidence

ORD record
ord-d91c54e577654fe58442815c1e31c430
Source dataset
uspto-grants-2015_12
Patent number
US09221826B2

Reaction notes

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