Water → HCID 90449618, compound

HRID 1411258Notes

Reaction equation

HRID 1411258 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[S:9][C:10]([S:13][CH:14]([CH3:20])[C:15](OCC)=[O:16])=[CH:11][N:12]=1.S([O-])([O-])(=O)=O.[Na+].[Na+].O>O1CCCC1>[NH2:7][C:8]1[S:9][C:10]([S:13][CH:14]([CH3:20])[CH2:15][OH:16])=[CH:11][N:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 86610213(2-Aminothiazole-5-ylsulfanyl)-propionic acid ethyl ester

Product 1

HCID 90449618HCID 90449618, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (97 mg, 2.56 mmol) was suspended in tetrahydrofuran (5 mL). Thereafter, under cooling on ice, a tetrahydrofuran (6 mL) solution of ethyl 2-((2-aminothiazol-5-yl)thio)propanoate (0.2 g, 0.85 mmol) was added to the obtained suspension, and the thus obtained mixture was then stirred for 30 minutes. Thereafter, sodium sulfate and water were added to the reaction solution, and the obtained mixture was then stirred. Insoluble matters were removed by filtration, and the filtrate was then concentrated in vacuo. The obtained residue was purified by preparative thin-layer chromatography (chloroform:methanol=5:1) to obtain 2-((2-aminothiazol-5-yl)thio)propan-1-ol (103 mg, 63%) in the form of a yellow oily product.

Workup

  1. temperatureThereafter, under cooling on ice
  2. stirringthe obtained mixture was then stirred
  3. customInsoluble matters were removed by filtration
  4. concentrationthe filtrate was then concentrated in vacuo
  5. customThe obtained residue was purified by preparative thin-layer chromatography (chloroform:methanol=5:1)

Sources & evidence

ORD record
ord-b260f7e215664af4ba97807ad94cd455
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

Loading…