Water → HCID 68314830, compound

HRID 513096Notes

Reaction equation

HRID 513096 reaction equation
[CH3:1][O:2][C:3]1[CH:33]=[CH:32][C:6]([CH2:7][N:8]2[C:13](=[O:14])[CH:12](C(OC)=O)[C:11](=[O:19])[C:10]3([CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]3)[CH2:9]2)=[CH:5][CH:4]=1.O>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:13](=[O:14])[CH2:12][C:11](=[O:19])[C:10]3([CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:29])([CH3:31])[CH3:30])=[O:26])[CH2:21][CH2:20]3)[CH2:9]2)=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 962WaterHCID 68315017HCID 68315017, compound

Product 1

HCID 68314830HCID 68314830, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Crude product A3 was dissolved in acetonitrile (50 mL) and water (50 mL) and stirred for 4 h at 80° C. The acetonitrile was evaporated off and the solids were filtered off, washed with water and taken up in DCM. The organic phase was dried over Na2SO4 and concentrated in vacuo. The product A4 (1.57 g) was obtained as a white solid. Overall yields (A2 to A4) are 70%. 1H NMR (400 MHz, CDCl3, 300K): δ=1.23 (2H, m), 1.41 (9H, s), 1.76 (2H, m), 3.13 (2H, m), 3.26 (2H, s), 3.37 (2H, m), 3.39 (2H, s), 3.81 (3H, s), 4.58 (2H, s), 6.87 (2H, d, J=8.6 Hz), 7.22 (d, J=8.6 Hz). 13C NMR (100 MHz, CDCl3, 300K): δ=28.8, 30.0, 46.3, 47.1, 49.8, 51.7, 55.7, 80.2, 114.6, 128.4, 130.5, 154.9, 159.8, 166.4, 206.8. MS (ES) C22H30N2O5 requires: 402. found: 425.2 [M+Na]+.

Workup

  1. customThe acetonitrile was evaporated off
  2. filtrationthe solids were filtered off
  3. washwashed with water
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6757cd7ab6bc4755a6b52ecc21e842f0
Source dataset
uspto-grants-2015_08
Patent number
US09102676B2

Reaction notes

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