Ammonium Chloride → HCID 90036907, compound

HRID 1055380Notes

Reaction equation

HRID 1055380 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][S:14][C:15]1[C:20]([N+:21]([O-])=O)=[CH:19][CH:18]=[CH:17][C:16]=1[N+:24]([O-])=O)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH4+].[Cl-]>[Zn].CO.O>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][S:14][C:15]1[C:16]([NH2:24])=[CH:17][CH:18]=[CH:19][C:20]=1[NH2:21])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 90037127HCID 90037127, compound

Product 1

HCID 90036907HCID 90036907, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of (R)-2-tert-butoxycarbonylamino-3-(2,6-dinitro-phenylsulfanyl)-propionic acid (1.7 g, 4.4 mmol) in 3:1 v/v MeOH/H2O (80 mL) containing NH4Cl (7.0 g, 130 mmol) was added Zn dust (5.7 g, 87.2 mmol) and the resulting mixture was stirred for 1 h. The mixture was filtered through a pad of Celite, the filtrate volume was reduced in vacuuo and acidified to pH 4 with 1.0 M HCl. The mixture was extracted with EtOAc, the combined extracts washed with H2O, brine, dried over Na2SO4, filtered and concentrated to give (R)-2-tert-butoxycarbonylamino-3-(2,6-diamino-phenylsulfanyl)-propionic acid (1.0 g) which was used without purification.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. extractionThe mixture was extracted with EtOAc
  3. washthe combined extracts washed with H2O, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a12b24e63ee84c8f83ada4edb3e1dab1
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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