Benzyl Bromide → HCID 10891827, compound

HRID 1051344Notes

Reaction equation

HRID 1051344 reaction equation
Cl.[NH2:2][C@@H:3]([CH3:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5].C([O-])([O-])=O.[K+].[K+].Br[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC#N>[CH2:17]([N:2]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C@@H:3]([CH3:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 2724356L-Alanine, ethyl ester, hydrochloride (1:1)

Product 1

HCID 10891827HCID 10891827, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of (S)-ethyl 2-aminopropanoate hydrochloride (4.59 g, 30.0 mmol) and K2CO3 (12.4 g, 90.0 mmol) in MeCN was added (bromomethyl)benzene (12.9 g, 75.0 mmol) at RT. The mixture was stirred at 70° C. for 14 h. The reaction mixture was quenched with aq. NH4Cl. After concentration, the aqueous layer was extracted with EtOAc. The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with petroleum ether/EtOAc (100:1) to afford 8.8 g (98%) of (S)-ethyl 2-(dibenzylamino)propanoate (26): LCMS (ESI) m/z: 298.2 [M+11]+.

Workup

  1. customThe reaction mixture was quenched with aq. NH4Cl
  2. concentrationAfter concentration
  3. extractionthe aqueous layer was extracted with EtOAc
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by SiO2 chromatography
  8. washeluting with petroleum ether/EtOAc (100:1)

Sources & evidence

ORD record
ord-df083a09ac2c46a3a1a0bc53a6b5baf5
Source dataset
uspto-grants-2016_07
Patent number
US09388171B2

Reaction notes

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