Diisopropylethylamine → HCID 178518189, compound

HRID 1620655Notes

Reaction equation

HRID 1620655 reaction equation
Cl.[NH2:2][C@@H:3]1[CH2:7][O:6][CH2:5][C@H:4]1[OH:8].S=[C:10]1[CH2:14][S:13][C:12](=[O:15])[NH:11]1.C(N(C(C)C)C(C)C)C>C(O)C>[OH:8][C@@H:4]1[CH2:5][O:6][CH2:7][C@H:3]1[NH:2][C:10]1[CH2:14][S:13][C:12](=[O:15])[N:11]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 15395954-Sulfanylidene-1,3-thiazolidin-2-oneHCID 70031001(3S,4R)-4-AMINOTETRAHYDROFURAN-3-OL HYDROCHLORIDE

Product 1

HCID 178518189HCID 178518189, compoundYield 40.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of trans-4-aminotetrahydrofuran-3-ol hydrochloride (1.00 g) in ethanol (30 mL) were added 4-thioxo-1,3-thiazolidin-2-one (954 mg) and N-ethyl-N-(1-methylethyl)propan-2-amine (3.87 mL), and the mixture was heated under reflux overnight. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methanol/ethyl acetate) to give the title compound (591 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (methanol/ethyl acetate)

Sources & evidence

ORD record
ord-763f4219635d4b32804b50e3085f579e
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

Loading…