Chloro-N,N-diethylacetamide → HCID 59202053, compound

HRID 1624192Notes

Reaction equation

HRID 1624192 reaction equation
C(/[C:5](=[CH:9]\[C:10]([OH:12])=[O:11])/[C:6]([OH:8])=[O:7])(C)(C)C.[CH2:13]([N:15]([CH2:20][CH3:21])[C:16](=[O:19])[CH2:17]Cl)[CH3:14].C(=O)([O-])O.[Cs+]>CN1CCCC1=O>[CH2:13]([N:15]([CH2:20][CH3:21])[C:16]([CH2:17][O:12][C:10](/[CH:9]=[CH:5]/[C:6]([OH:8])=[O:7])=[O:11])=[O:19])[CH3:14]

Participants

5

Reactant 3

HCID 16844Chloro-N,N-diethylacetamideHCID 2734983Cesium bicarbonateHCID 86639359HCID 86639359, compound

Product 1

HCID 59202053HCID 59202053, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Following general procedure A, mono tert-butyl fumaric acid (0.70 g, 4.06 mmol) was reacted with N,N-diethyl chloroacetamide (0.55 mL, 0.60 g, 4.06 mmol) and CsHCO3 (0.93 g, 4.87 mmol) at ca. 55° C. in N-methylpyrrolidinone (NMP). After isolation and purification, the crude material was reacted in 50 vol-% trifluoroacetic acid (TFA) in dichloromethane (DCM). The free acid was purified by mass-guided preparative HPLC to afford 0.051 g (6% yield) of the title compound (48) as a white solid. 1H NMR (CD3CN, 400 MHz): δ 6.90-6.82 (m, 2H), 4.88 (s, 2H), 3.40-3.32 (q, J=6.8 Hz, 2H), 3.31-3.27 (q, J=6.8 Hz, 2H), 1.22-1.18 (t, J=7.6 Hz, 3H), 1.11-1.07 (t, J=6.8 Hz, 3H). MS (ESI): m/z=230.03 (M+H)+, 228.07 (M−H)−.

Workup

  1. customAfter isolation and purification
  2. customthe crude material was reacted in 50 vol-% trifluoroacetic acid (TFA) in dichloromethane (DCM)
  3. customThe free acid was purified by mass-guided preparative HPLC

Sources & evidence

ORD record
ord-c2b1c6a28b1d4939b0f220dcfad2720a
Source dataset
uspto-grants-2014_07
Patent number
US08778991B2

Reaction notes

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