Tetrahydrofuran → tert-Butyl 2-thioureidoacetate

HRID 1110456Notes

Reaction equation

HRID 1110456 reaction equation
C1COCC1.Cl.[C:7]([O:11][C:12](=[O:15])[CH2:13][NH2:14])([CH3:10])([CH3:9])[CH3:8].C(N(CC)CC)C.C1C([N:29]=[C:30]=[S:31])=CC2C(OC3(C4C=CC(O)=CC=4OC4C=C(O)C=CC3=4)C=2C=1)=O>C(=O)([O-])[O-].[Na+].[Na+].CN(C=O)C.C(Cl)(Cl)Cl>[C:7]([O:11][C:12](=[O:15])[CH2:13][NH:14][C:30]([NH2:29])=[S:31])([CH3:10])([CH3:9])[CH3:8]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 18730Fluorescein 5-isothiocyanateHCID 2725036Glycine tert-butyl ester hydrochloride

Product 1

HCID 57225720tert-Butyl 2-thioureidoacetate

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 10340Sodium CarbonateSolvent

Procedure

To a 50 ml round bottom flask equipped with magnetic stirring bar was added a solvent mixture (10 ml THF, 5 ml of CHCl3, and 5 ml of DMF) and 168 mg (1 mmole) of glycine t-butyl ester hydrochloride. The solution was cooled by an ice-water bath and 415 ml (3 mmoles) of triethylamine was added. To the above mixture was added FITC (fluorescein isothiocyanate, 1 mmole, 385 mg) in small portions over 3 hours. The reaction mixture was allowed to stir overnight and then concentrated to a red-brown oil that was dissolved in 100 ml ethyl acetate and washed with 5 ml water followed by 2-10 ml portions of saturated brine. Preparative tlc on silica with 10% methanol in chloroform and a trace of acetic acid gave tlc pure material, 240 mg. Molar extinction coefficient: ε=79,500 M- cm-1 (λmax=494 nm) in 0.5M sodium carbonate, pH 9.53. Anal. calc for C27H24N2O7S·H2O: C, 60.22; H, 4.83; N, 5.20; S, 5.95. Found: C, 60.16; H, 4.85; N, 5.01; S, 6.15.

Workup

  1. customTo a 50 ml round bottom flask equipped with magnetic stirring bar
  2. temperatureThe solution was cooled by an ice-water bath
  3. concentrationconcentrated to a red-brown oil that
  4. dissolutionwas dissolved in 100 ml ethyl acetate
  5. washwashed with 5 ml water
  6. customPreparative tlc on silica with 10% methanol in chloroform and a trace of acetic acid gave tlc pure material, 240 mg

Sources & evidence

ORD record
ord-dda9b9ee9b524a16907489d81939b42d
Source dataset
uspto-grants-1990_12
Patent number
US04975532

Reaction notes

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