2,5-dioxopyrrolidin-1-yl 3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanoate → 3-(2,5-dioxo-2H-pyrrol-1(5H)-yl)-N-(3-(1,1,1,3,3,3-hexafluoro-2-(methoxy-methoxy)propan-2-yl)-4-(tributylstannyl)benzyl)-N-methylpropanamide

HRID 926934Notes

Reaction equation

HRID 926934 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]([C:12]1[CH:13]=[C:14]([CH2:31][NH:32][CH3:33])[CH:15]=[CH:16][C:17]=1[Sn:18]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH2:21][CH3:22])([O:8][CH2:9][O:10][CH3:11])[C:4]([F:7])([F:6])[F:5].C1C(=O)N(O[C:44]([CH2:46][CH2:47][N:48]2[C:53](=[O:54])[CH:52]=[CH:51][C:49]2=[O:50])=[O:45])C(=O)C1>C(#N)C>[O:54]=[C:53]1[CH:52]=[CH:51][C:49](=[O:50])[N:48]1[CH2:47][CH2:46][C:44]([N:32]([CH2:31][C:14]1[CH:15]=[CH:16][C:17]([Sn:18]([CH2:23][CH2:24][CH2:25][CH3:26])([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:19][CH2:20][CH2:21][CH3:22])=[C:12]([C:3]([O:8][CH2:9][O:10][CH3:11])([C:4]([F:5])([F:6])[F:7])[C:2]([F:1])([F:34])[F:35])[CH:13]=1)[CH3:33])=[O:45]

Participants

4

Reactant 2

HCID 46205972,5-dioxopyrrolidin-1-yl 3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanoateHCID 87358059HCID 87358059, compound

Product 1

HCID 873590013-(2,5-dioxo-2H-pyrrol-1(5H)-yl)-N-(3-(1,1,1,3,3,3-hexafluoro-2-(methoxy-methoxy)propan-2-yl)-4-(tributylstannyl)benzyl)-N-methylpropanamideYield 81%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 14 (86 mg, 138 μmol) was dissolved in anhydrous acetonitrile (2 mL) and 3-(Maleimido)propionic acid N-hydroxysuccinimide ester (44 mg, 166 mmol) was added. The mixture was stirred overnight at room temperature, the solvent removed under reduced pressure and the residue purified over silica gel using chloroform/methanol (98/2) as eluant to give 86 mg (111 μmol, 81% yield) of a colorless oil.

Workup

  1. customthe solvent removed under reduced pressure
  2. customthe residue purified over silica gel

Sources & evidence

ORD record
ord-43ab1602f6f2477299f955d41861f645
Source dataset
uspto-grants-2016_03
Patent number
US09290421B2

Reaction notes

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