Tert-butyl [4'-(2,4-dioxothiazolidin-5-ylidenemethyl)biphenyl-3-ylmethyl]methylcarbamate → Tert-butyl [4'-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]methylcarbamate

HRID 1592971Notes

Reaction equation

HRID 1592971 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[C:4](=[CH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][N:22]([CH3:30])[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:16]=3)=[CH:11][CH:10]=2)[S:3]1>O1CCOCC1>[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][N:22]([CH3:30])[C:23](=[O:29])[O:24][C:25]([CH3:26])([CH3:28])[CH3:27])[CH:16]=3)=[CH:13][CH:14]=2)[S:3]1

Participants

3

Reactant 1

HCID 86598938Tert-butyl [4'-(2,4-dioxothiazolidin-5-ylidenemethyl)biphenyl-3-ylmethyl]methylcarbamate

Product 1

HCID 10202718Tert-butyl [4'-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]methylcarbamate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

30 g (70.7 mmol) of tert-butyl [4′-(2,4-dioxothiazolidin-5-ylidenemethyl)biphenyl-3-ylmethyl]methylcarbamate in 500 ml of dioxane are introduced into a three-necked flask. The reaction medium is degassed, 30 g of palladium on carbon (10%) are added and the mixture is hydrogenated at a pressure of 3 bar at 60° C. The reaction medium is filtered, evaporated off and the residue obtained is purified by chromatography on a silica column eluted with a dichloromethane and methanol (99-1) mixture. 18 g (60%) of the expected product are recovered after evaporation of the solvents.

Workup

  1. customThe reaction medium is degassed
  2. addition30 g of palladium on carbon (10%) are added
  3. customis hydrogenated at a pressure of 3 bar at 60° C
  4. filtrationThe reaction medium is filtered
  5. customevaporated off
  6. customthe residue obtained
  7. customis purified by chromatography on a silica column
  8. washeluted with a dichloromethane and methanol (99-1) mixture
  9. custom18 g (60%) of the expected product are recovered
  10. customafter evaporation of the solvents

Sources & evidence

ORD record
ord-826a8c00eff9490494f0ccefa755863c
Source dataset
uspto-grants-2007_11
Patent number
US07294639B2

Reaction notes

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