Ammonia → HCID 67411024, compound

HRID 1802091Notes

Reaction equation

HRID 1802091 reaction equation
[CH:1]([C:3]1[CH:8]=[C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:6]=[CH:5][C:4]=1[NH:17][C:18](=O)[C@H:19]([CH3:25])[CH2:20][O:21][CH2:22][O:23][CH3:24])=O.CO.[NH3:29]>>[CH2:10]([O:9][C:7]1[CH:8]=[C:3]2[C:4](=[CH:5][CH:6]=1)[N:17]=[C:18]([C@H:19]([CH3:25])[CH2:20][O:21][CH2:22][O:23][CH3:24])[N:29]=[CH:1]2)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 73671013HCID 73671013, compound

Product 1

HCID 67411024HCID 67411024, compoundYield 75.1%

Conditions

Temperature
-78 °C

Procedure

(R)—N-(2-Formyl-4-heptyloxyphenyl)-3-methoxymethoxy-2-methylpropanamide (2.50 g, 0.00684 mol) was dissolved in methanol (200 mL, 5 mol), and cooled to −78° C., followed by ammonia (20 g, 1 mol) bubbling for 3 hours. The reaction mixture was then transferred to a pre-cooled high pressure reactor, and heated at 130° C. for 15 hours (310 psi). Solvent was removed, and the crude mixture was purified via chromatography (SiO2, 40 g, 0-60% ethyl acetate/hexanes) to give the desired product (1.78 g, 75%). 1H NMR (CHLOROFORM-d) δ: 9.26 (s, 1H), 7.90 (d, J=9.3 Hz, 1H), 7.52 (dd, J=9.2, 2.6 Hz, 1H), 7.10 (d, J=2.3 Hz, 1H), 4.55-4.68 (m, 2H), 4.02-4.16 (m, 3H), 3.85 (dd, J=9.4, 6.4 Hz, 1H), 3.45-3.61 (m, 1H), 3.27 (s, 3H), 1.79-1.95 (m, 2H), 1.45-1.57 (m, 2H), 1.27-1.45 (m, 9H), 0.91 (t, J=6.7 Hz, 3H). MS (M+1): 347.30.

Workup

  1. custombubbling for 3 hours
  2. customThe reaction mixture was then transferred to a pre-cooled high pressure reactor
  3. temperatureheated at 130° C. for 15 hours (310 psi)
  4. customSolvent was removed
  5. customthe crude mixture was purified via chromatography (SiO2, 40 g, 0-60% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-5799df6f0cef415f90ffb78c018cfec3
Source dataset
uspto-grants-2013_01
Patent number
US08349849B2

Reaction notes

Loading…