Boc-L-3-Bromophenylalanine → 468740-94-5

HRID 339953Notes

Reaction equation

HRID 339953 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C@H:9]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:10](O)=[O:11])[CH:5]=[CH:6][CH:7]=1>C1COCC1>[C:17]([O:16][C:14](=[O:15])[NH:13][C@@H:9]([CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[CH2:10][OH:11])([CH3:20])([CH3:18])[CH3:19]

Participants

3

Reactant 1

HCID 2734476Boc-L-3-Bromophenylalanine

Product 1

HCID 58666623468740-94-5Yield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (2S)-3-(3-bromophenyl)-2-[(tert-butoxycarbonyl)amino]propanoic acid (Chem-Impex) (15 g, 44 mmol) in tetrahydrofuran (31 mL, 380 mmol) with stirring, 1.0 M borane-THF complex in THF (130 mL) was added dropwise to keep temperature at 0° C. (about 15 min). After addition the reaction mixture was stirred at room temperature for 1 h, cooled with an ice-bath, quenched with AcOH:MeOH (1:5, 70 mL), and partitioned between saturated aqueous NaHCO3 solution and DCM, dried over sodium sulfate and evaporated under reduced pressure to give 13.2 g (92% yield) of the crude desired product, which was used in the next reaction with no further purification. LC-MS found: 330.1 (M+H)+.

Workup

  1. customat 0° C.
  2. custom(about 15 min)
  3. additionAfter addition the reaction mixture
  4. temperaturecooled with an ice-bath
  5. customquenched with AcOH:MeOH (1:5, 70 mL)
  6. custompartitioned between saturated aqueous NaHCO3 solution and DCM
  7. dry with materialdried over sodium sulfate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-20e05254cd20429b9157601b87c64345
Source dataset
uspto-grants-2014_11
Patent number
US08895571B2

Reaction notes

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