1,2-Dichloroethane → [1-(2-Fluoro-benzyl)-2-oxo-2-thiazolidin-3-yl-ethyl]-carbamic acid tert-butyl ester

HRID 1872194Notes

Reaction equation

HRID 1872194 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[F:20])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[S:21]1[CH2:25][CH2:24][NH:23][CH2:22]1.C(Cl)CCl>CN(C)C1C=CN=CC=1.ClCCl.C(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[F:20])[C:10](=[O:12])[N:23]1[CH2:24][CH2:25][S:21][CH2:22]1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 3

HCID 111,2-DichloroethaneHCID 10444ThiazolidineHCID 2756793HCID 2756793, compound

Product 1

HCID 21710700[1-(2-Fluoro-benzyl)-2-oxo-2-thiazolidin-3-yl-ethyl]-carbamic acid tert-butyl esterYield 62.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-tert-butoxycarbonylamino-3-(2-fluoro-phenyl)-propionic acid (0.50 g, 1.77 mmol), thiazolidine (0.15 mL, 1.94 mmol) and 4-dimethylamino-pyridine (0.21 g, 1.77 mmol) in dichloromethane (15 mL) was added EDC (0.44 g, 2.31 mmol). The reaction mixture was stirred at room temperature overnight, diluted with chloroform, washed with 2 N HCl, water and brine, dried over magnesium sulfate and concentrated. The product was purified by flash-chromatography (30% acetone in hexanes) and obtained as a colorless solid (0.39 g, 62%, mp 133-134° C.).

Workup

  1. washwashed with 2 N HCl, water and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe product was purified by flash-chromatography (30% acetone in hexanes)

Sources & evidence

ORD record
ord-804b8cfa7fe0401491a298f060c26d67
Source dataset
uspto-grants-2000_08
Patent number
US06107329

Reaction notes

Loading…