Triethylamine → Bromoacetylphenylalanine ethyl ester

HRID 215737Notes

Reaction equation

[Br:1][CH2:2][C:3](Br)=[O:4].[CH2:6]([O:8][C:9](=[O:19])[C@H:10]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[NH2:11])[CH3:7].C(N(CC)CC)C>C(Cl)(Cl)Cl.C(Cl)Cl.CCCCCC>[CH2:6]([O:8][C:9](=[O:19])[C@H:10]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[NH:11][C:3](=[O:4])[CH2:2][Br:1])[CH3:7]

Participants

Conditions

Temperature: -30 °C

Procedure

Under argon, bromoacetyl bromide (0.89 g, 10.2 mmol) in chloroform (10 mL) was added dropwise to a mixture of chloroform (40 mL), L-phenylalanine ethyl ester (2.3 g, 10 mmol), and triethylamine (3 mL), which was pre-cooled to −30° C. The mixture was stirred at r.t. for a further 2 hrs, and then washed with aqueous saturated potassium carbonate solution and water, then dried over sodium sulfate. The solvents were removed under reduced pressure, giving a dark oil, which was dissolved in a mixture of DCM (100 mL) and hexane (300 mL), form which a crystalline solid deposited. The crystals were dried in air, giving colourless needles (2.7 g, 79%). 1H-NMR (CDCl3): 7.29-7.31 (3H, m, Ar), 7.11-7.16 (2H, m, Ar), 4.79-4.89 (1H, m, α-H), 4.20 (2H, q, J 7.2, OCH2CH3), 3.86 (2H, s, BrCH2), 3.16 (2H, d, J 5.8, ArCH2), 1.26 (3H, t, J 7.2, OCH2CH3). m/z (ES+): 336 [M+Na]+.

Workup

washwashed with aqueous saturated potassium carbonate solution and water
dry with materialdried over sodium sulfate
customThe solvents were removed under reduced pressure
customgiving a dark oil, which
customThe crystals were dried in air

Sources & evidence

ORD record: ord-1b3237a8e0554f4c968068cbf6e8d572
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193174B2

Reaction notes

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