Sodium Hydroxide → HCID 70873984, compound

HRID 2208811Notes

Reaction equation

HRID 2208811 reaction equation
[CH2:1]([N:3]([CH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)[C:4]1[CH:5]=[C:6]([CH:15]2[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:16]2)[CH:7]=[C:8]([C:11]([O:13]C)=[O:12])[C:9]=1[CH3:10])[CH3:2].[OH-].[Na+]>C1COCC1.CO>[C:22]([O:21][C:19]([N:17]1[CH2:18][CH:15]([C:6]2[CH:5]=[C:4]([N:3]([CH2:1][CH3:2])[CH:26]3[CH2:27][CH2:28][O:29][CH2:30][CH2:31]3)[C:9]([CH3:10])=[C:8]([CH:7]=2)[C:11]([OH:13])=[O:12])[CH2:16]1)=[O:20])([CH3:24])([CH3:25])[CH3:23]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70913338HCID 70913338, compound

Product 1

HCID 70873984HCID 70873984, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of tert-butyl 3-{3-[ethyl(oxan-4-yl)amino]-5-(methoxycarbonyl)-4-methylphenyl}azetidine-1-carboxylate (78 mg, 0.18 mmol) in THF (2 ml) and MeOH (0.1 ml) was added 2M NaOH solution (0.9 ml, 1.8 mmol) and the reaction was stirred at room temperature for 16 h followed by heating at 50° C. for 22 h. The reaction was cooled to room temperature and the solvent removed in vacuo after which the aqueous solution was adjusted to pH5 using 1M HCl. The product was extracted into DCM (2×50 ml), dried with Na2SO4 and filtered to afford the title compound as a colourless oil (54 mg, 72%). LC-MS 100%, 1.70 min (3.5 minute LC-MS method), m/z=419.2, 1H NMR (500 MHz, MeOD) δ 7.77 (s, 1H), 7.55 (s, 1H), 4.36 (t, J=8.2 Hz, 2H), 3.90 (d, J=27.0 Hz, 5H), 3.71 (t, J=6.5 Hz, 1H), 3.36 (t, J=11.3 Hz, 3H), 2.55 (s, 3H), 1.92-1.81 (m, 1H), 1.64 (d, J=55.8 Hz, 3H), 1.49-1.42 (m, 10H), 0.93 (s, 3H).

Workup

  1. temperatureby heating at 50° C. for 22 h
  2. temperatureThe reaction was cooled to room temperature
  3. customthe solvent removed in vacuo after which the aqueous solution
  4. extractionThe product was extracted into DCM (2×50 ml)
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-f4be4f215303473b81ec89bf87971043
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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