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 584958Notes

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.[H][H]>O1CCOCC1.[Pd]>[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

Conditions

Temperature: 50 °C

Procedure

30 g (71 mmol) of tert-butyl [4′-(2,4-dioxothiazolidin-5-ylidenemethyl)biphenyl-3-ylmethyl]methylcarbamate in 500 ml of dioxane are placed in a reactor. The reaction medium is degassed, followed by addition of g (1 equivalent by mass) of 10% palladium-on-charcoal. The system is placed under 3 bar of hydrogen and heated at 50° C. for seven hours. The reaction medium is filtered through Celite and evaporated, and the residue obtained is purified by chromatography on a column of silica with an fluent mixture of dichloromethane and methanol (98/2). After evaporation of the solvents, 18 g (60%) of the expected product are collected.

Workup

customThe reaction medium is degassed
filtrationThe reaction medium is filtered through Celite
customevaporated
customthe residue obtained
customis purified by chromatography on a column of silica with an fluent mixture of dichloromethane and methanol (98/2)
customAfter evaporation of the solvents, 18 g (60%) of the expected product
customare collected

Sources & evidence

ORD record: ord-9dd99886a2164138b60b9ef2fd3bcbfc
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06927228B2

Reaction notes

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