Dicyclohexylcarbodiimide → N-(3-Acetylthio-2-methylpropanoyl)-N-tetrahydrofurfurylglycine tert-butyl ester

HRID 280112Notes

Reaction equation

HRID 280112 reaction equation
[C:1]([O:5][C:6](=[O:15])[CH2:7][NH:8][CH2:9][CH:10]1[O:14][CH2:13][CH2:12][CH2:11]1)([CH3:4])([CH3:3])[CH3:2].[C:16]([S:19][CH2:20][CH:21]([CH3:25])[C:22](O)=[O:23])(=[O:18])[CH3:17].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:15])[CH2:7][N:8]([C:22](=[O:23])[CH:21]([CH3:25])[CH2:20][S:19][C:16](=[O:18])[CH3:17])[CH2:9][CH:10]1[O:14][CH2:13][CH2:12][CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 1180733-(Acetylthio)-2-methylpropanoic acidHCID 13505723HCID 13505723, compound

Product 1

HCID 13505724N-(3-Acetylthio-2-methylpropanoyl)-N-tetrahydrofurfurylglycine tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-tetrahydrofurfurylglycine tert-butyl ester (6.6 g, 0.0307 mol) and 3-acetylthio-2-methylpropionic acid (5.3 g, 0.0307 mol) in dry methylene chloride (150 ml) chilled in an ice bath was added dicyclohexylcarbodiimide (6.7 g, 0.0325 mol). The resulting mixture was stirred with cooling for 30 minutes and then overnight at room temperature. Precipitated dicyclohexylurea was filtered and washed with a small amount of methylene chloride. Concentration of the filtrate afforded crude product as a thick yellow oil which was used without further purification.

Workup

  1. temperaturewith cooling for 30 minutes
  2. customovernight
  3. customat room temperature
  4. filtrationPrecipitated dicyclohexylurea was filtered
  5. washwashed with a small amount of methylene chloride
  6. customConcentration of the filtrate afforded crude product as a thick yellow oil which
  7. customwas used without further purification

Sources & evidence

ORD record
ord-37331632028f490fb3786530f10b2b0a
Source dataset
uspto-grants-1986_05
Patent number
US04588734

Reaction notes

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