Boc-L-3-Bromophenylalanine → 3-Bromo-L-phenylalanine

HRID 1364096Notes

Reaction equation

HRID 1364096 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C@H:9]([NH:13]C(OC(C)(C)C)=O)[C:10]([OH:12])=[O:11])[CH:5]=[CH:6][CH:7]=1>Cl.O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH2:8][C@@H:9]([C:10]([OH:12])=[O:11])[NH2:13]

Participants

4

Reactant 1

HCID 2734476Boc-L-3-Bromophenylalanine

Product 1

HCID 27622593-Bromo-L-phenylalanineYield 90.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

(2S)-3-(3-Bromophenyl)-2-(tert-butoxycarbonylamino)propionic acid (5.0 g, 14.5 mmol) was suspended in 4M HCl in 1,4-dioxane (75 mL) and stirred for 16 h at r.t. The white precipitate was filtered and washed with Et2O to give the title compound as a white solid (3.2 g, 89%) that required no farther purification. δH(CDCl3) 8.32 (2H, s), 7.50-7.48 (2H, m), 7.34-7.29 (2H, m), 4.22 (1H, t, J 6.2 Hz), 3.13-3.11 (2H, m). An exchangeable proton was not observed.

Workup

  1. filtrationThe white precipitate was filtered
  2. washwashed with Et2O

Sources & evidence

ORD record
ord-5bee28ace9504a60b98c582f4f2e8a14
Source dataset
uspto-grants-2011_02
Patent number
US07888344B2

Reaction notes

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