HCID 68314955, compound → HCID 68315272, compound

HRID 1618958Notes

Reaction equation

HRID 1618958 reaction equation
[O:1]=[C:2]1[CH:18](C(OC)=O)[C:17](=[O:23])[C:5]2([CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7][CH2:6]2)[CH2:4][NH:3]1>C(#N)C.O>[O:1]=[C:2]1[CH2:18][C:17](=[O:23])[C:5]2([CH2:9][N:8]([C:10]([O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:11])[CH2:7][CH2:6]2)[CH2:4][NH:3]1

Participants

3

Reactant 1

HCID 68314955HCID 68314955, compound

Product 1

HCID 68315272HCID 68315272, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

A solution of D5 (1.90 mmol, 0.62 g) in 40 mL acetonitrile/water (1/1) was refluxed for 5 hours. The reaction mixture was evaporated in vacuo. The crude product was purified by flash silicagel chromatography (DCM/MeOH=95/5) yielding 0.34 g of a yellow oil (66%). 1H-NMR (400 MHz, CDCl3, 300K): δ=1.46 (9H, s), 1.88 (1H, m), 2.26 (1H, m), 3.50 (8H, m), 6.70 (1H, br d, 34.8 Hz); MS (ES) C13H20N2O4 requires: 268. found: 269.4 [M+H]+.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customThe crude product was purified by flash silicagel chromatography (DCM/MeOH=95/5)

Sources & evidence

ORD record
ord-c13828001c744135ab2bd6199b0dadb0
Source dataset
uspto-grants-2014_07
Patent number
US08772286B2

Reaction notes

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