1,2-Dichloroethane → HCID 86756430, compound

HRID 636007Notes

Reaction equation

HRID 636007 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][CH2:15][NH:16][CH2:17][N:18]=[N:19][N+:20]([O-:22])=[O:21])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:23][C:24]1[S:25][CH:26]=[CH:27][N:28]=1.C(Cl)CCl.[Cl-].[Na+]>CN(C=O)C>[S:25]1[CH:26]=[CH:27][N:28]=[C:24]1[NH:23][C:10](=[O:12])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:14][CH2:15][NH:16][CH2:17][N:18]=[N:19][N+:20]([O-:22])=[O:21]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 21552-AminothiazoleHCID 5234Sodium ChlorideHCID 86756431HCID 86756431, compound

Product 1

HCID 86756430HCID 86756430, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (2S)-2-tert-butoxycarbonylamino-5-(nitroimino-amino)methylaminopentanoic acid (5.00 g, 15.6 mmol) and 2-aminothiazole (1.72 g, 17.2 mmol) in DMF (16 mL) is added EDC (3.30 g, 17.2 mmol). The solution is allowed to stir for 4 h then added to half-saturated aqueous sodium chloride solution and extracted with EtOAc. The combined organic extracts are washed with 1 N sodium bisulfate, 5% aqueous sodium bicarbonate, saturated aqueous sodium chloride, and dried over magnesium sulfate. Concentration in vacuo provides (2S)-2-tert-butoxycarbonylamino-5-(nitroimino-amino)methylaminopentanoic acid 1,3-thiazol-2-ylamide as a solid (2.28 g, 36%).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic extracts are washed with 1 N sodium bisulfate, 5% aqueous sodium bicarbonate, saturated aqueous sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-a359d86b47734f01add25fa7b1ec96e7
Source dataset
uspto-grants-2001_02
Patent number
US06191150B1

Reaction notes

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