Sodium Hydroxide → (2R)-3-(4-bromophenyl)-2-{[(tert-butoxy)carbonyl]amino}propanoic acid

HRID 2275485Notes

Reaction equation

HRID 2275485 reaction equation
[NH2:1][C@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].[OH-].[Na+].[O:16](C(OC(C)(C)C)=O)[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=O>CC#N.O>[Br:13][C:10]1[CH:9]=[CH:8][C:7]([CH2:6][C@@H:2]([NH:1][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:16])[C:3]([OH:5])=[O:4])=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 90495Di-tert-butyl dicarbonateHCID 671215(R)-2-amino-3-(4-bromophenyl)propionic acid

Product 1

HCID 7020327(2R)-3-(4-bromophenyl)-2-{[(tert-butoxy)carbonyl]amino}propanoic acidYield 93.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

To a solution of (R)-2-amino-3-(4-bromophenyl)propionic acid (50 g, 0.2 mol) in MeCN (700 mL) was added a solution of NaOH (16.4 g, 0.4 mol) in water (700 mL) at −5° C. After stirring for 10 minutes, a solution of (BOC)2O (44.7 g, 0.2 mol) in MeCN (100 mL) was added. The mixture was warmed to room temperature and stirred overnight. After evaporation of the MeCN, the residue was diluted with DCM (800 mL) and acidified with 1 M HCl to pH 2 at −5° C. The aqueous layer was extracted with DCM (3×200 mL). The combined organic layers were washed with saturated aqueous NaCl (500 mL), dried over anhydrous Na2SO4 and concentrated to yield the title compound as a white solid (64.2 g). LC-MS: [M+Na]:366, [2M+Na]:709.

Workup

  1. stirringstirred overnight
  2. customAfter evaporation of the MeCN
  3. additionthe residue was diluted with DCM (800 mL)
  4. customacidified with 1 M HCl to pH 2 at −5° C
  5. extractionThe aqueous layer was extracted with DCM (3×200 mL)
  6. washThe combined organic layers were washed with saturated aqueous NaCl (500 mL)
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3cc11813e2f14b62a71f621f6df96c6d
Source dataset
uspto-grants-2015_09
Patent number
US09126956B2

Reaction notes

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