Ammonium Chloride → (S)-3-(2-amino-6-bromophenoxy)-2-(tert-butoxycarbonylamino)propanoic acid

HRID 1055489Notes

Reaction equation

HRID 1055489 reaction equation
[Br:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-])=O)[C:3]=1[O:4][CH2:5][C@H:6]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:7]([OH:9])=[O:8].[NH4+].[Cl-]>CO.C1COCC1.[Zn]>[NH2:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:2]([Br:1])[C:3]=1[O:4][CH2:5][C@H:6]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:15])[CH3:16])=[O:12])[C:7]([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 67328353O-(2-bromo-6-nitrophenyl)-N-(tert-butoxycarbonyl)-L-serine

Product 1

HCID 90036994(S)-3-(2-amino-6-bromophenoxy)-2-(tert-butoxycarbonylamino)propanoic acidYield 97%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of (S)-3-(2-bromo-6-nitrophenoxy)-2-(tert-butoxycarbonylamino)propanoic acid (2.1 g, 5.18 mmol), zinc dust (3.39 g, 51.8 mmol) and NH4Cl (2.77 g, 51.8 mmol) in MeOH/THF 1:1 (40 mL) was stirred at RT until TLC indicated the reaction was complete. The mixture was then filtered and the filtrate concentrated. The residue was mixed with H2O/EtOAc (50 mL/50 mL) and extracted with EtOAc. The combined organic extracts were dried over MgSO4, filtered and the filtrate concentrated to afford (S)-3-(2-amino-6-bromophenoxy)-2-(tert-butoxycarbonylamino)propanoic acid (1.88 g, 97%) as an off-white foam which was used without purification.

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationthe filtrate concentrated
  3. additionThe residue was mixed with H2O/EtOAc (50 mL/50 mL)
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-f9452e4e73b244cea38dbf2b288ae1ed
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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