Diisopropylethylamine → HCID 58480331, compound

HRID 2403993Notes

Reaction equation

HRID 2403993 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]([NH:5][CH2:6][CH2:7][NH:8][CH2:9][CH3:10])=[O:4].CCN(C(C)C)C(C)C.[CH2:22]([O:29][C:30](N1C(=O)CCC1=O)=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[CH2:22]([O:29][C:30](=[O:31])[N:8]([CH2:9][CH3:10])[CH2:7][CH2:6][NH:5][C:3](=[O:4])[C:2]([F:11])([F:12])[F:1])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 3826287Benzyl 2,5-dioxopyrrolidine-1-carboxylateHCID 13429029HCID 13429029, compound

Product 1

HCID 58480331HCID 58480331, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of compound M (24.6 g, 82.4 mmol) and DIEA (14.3 ml, 82.4 mmol) in THF (100 ml) was cooled to ˜5° C., followed by the addition of a solution of N-(benzyloxycarbonyl)succinimide (20.3 g, 81.6 mmol) in THF (75 ml) dropwise over 20 min The temperature of the reaction mixture was raised to room temperature and stirring was continued for an additional 30 min. Solvents were evaporated and the residue was dissolved in EtOAc (500 ml). The organic layer was extracted with 5% aqueous NaHCO3 (2×100 ml) and brine (100 ml). The organic layer was evaporated to provide compound N (24.9 g, 78.2 mmol) as yellowish oil. LC-MS [M+H] 319.0 (C14H17F3N2O3+H, calc: 319.2). Compound N was used without further purification.

Workup

  1. customSolvents were evaporated
  2. dissolutionthe residue was dissolved in EtOAc (500 ml)
  3. extractionThe organic layer was extracted with 5% aqueous NaHCO3 (2×100 ml) and brine (100 ml)
  4. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-7dfaab7c029749fba5503ca93635926d
Source dataset
uspto-grants-2014_08
Patent number
US08802681B2

Reaction notes

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