HCID 86660752, compound → HCID 24988150, compound

HRID 1404842Notes

Reaction equation

HRID 1404842 reaction equation
CC(C)(O[C:5](=O)[N:6](C)[O:7][CH2:8][CH:9]([CH3:18])[O:10][C:11](=[O:17])[CH2:12][CH2:13][C:14]([OH:16])=[O:15])C>C(O)(C(F)(F)F)=O>[CH3:5][NH:6][O:7][CH2:8][CH:9]([O:10][C:11](=[O:17])[CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH3:18]

Participants

3

Reactant 1

HCID 86660752HCID 86660752, compound

Product 1

HCID 24988150HCID 24988150, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2,2,5,8-Tetramethyl-4,10-dioxo-3,6,9-trioxa-5-azatridecan-13-oic acid (227 mg, 0.744 mmol) was dissolved in 4 mL TFA. The reaction mixture was stirred at room temperature for 4 h and concentrated. The crude product was purified by silica gel flash column chromatography using 12% MeOH/dichloromethane as eluent. The desired product was obtained as a colorless gel (30 mg, 0.146 mmol, 20%). 1H NMR (CD3OD, 300 MHz): δ (ppm) 1.17 (d, 3H, J=6.6 Hz), 2.58 (s, 3H), 2.61 (s, 3H), 3.66 (d, 2H, J=5.4 Hz), 5.10-5.16 (m, 1H).

Workup

  1. concentrationconcentrated
  2. customThe crude product was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-7dcbc2a5922b40f6b644ba155dab54da
Source dataset
uspto-grants-2014_12
Patent number
US08916169B2

Reaction notes

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