Methanol → HCID 56643954, compound

HRID 71230Notes

Reaction equation

HRID 71230 reaction equation
[C:1]1([C:7]2([CH2:13][CH2:14][C:15]3[O:19][N:18]=[C:17]([C:20]4[CH:37]=[CH:36][C:23]([CH2:24][N:25]5[CH2:28][CH:27]([C:29]([O:31]C(C)(C)C)=[O:30])[CH2:26]5)=[CH:22][CH:21]=4)[N:16]=3)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO>Cl.O1CCOCC1>[C:1]1([C:7]2([CH2:13][CH2:14][C:15]3[O:19][N:18]=[C:17]([C:20]4[CH:21]=[CH:22][C:23]([CH2:24][N:25]5[CH2:28][CH:27]([C:29]([OH:31])=[O:30])[CH2:26]5)=[CH:36][CH:37]=4)[N:16]=3)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 887Methanol2×HCID 66692502Tert-butyl 1-(4-(5-(2-(1-phenylcyclohexyl)ethyl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylate

Product 1

HCID 56643954HCID 56643954, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

The glassy solid tert-butyl 1-(4-(5-(2-(1-phenylcyclohexyl)ethyl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylate was dissolved in 3 mL of 4N HCl in dioxane, and the mixture was stirred for 5 h. The reaction was followed by LC/MS and was evaporated and dried in vacuo. The residue was purified by prep. HPLC (Phenomenex S10 30×100 mm, 40 min gradient time, Detection Wave length 220 nm, Starting solvent: 10% aq. MeOH—0.1% TFA; Final solvent: 90% aq. MeOH—0.1% TFA) to give the 1-(4-(5-(2-(1-phenylcyclohexyl)ethyl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylic acid (47.5 mg, yield=21%) as a white solid. LC/MS: m/e 446.17 (M+H)+. 1H NMR (400 MHz, CD3OD): δ ppm 8.1 (d, J=8.28 Hz, 2H), 7.61 (d, J=8.28 Hz, 2H), 7.40-7.46 (m, 2H), 7.32-7.39 (m, 2H), 7.14-7.21 (m, 1H), 4.49 (s, 2H), 4.36 (d, J=7.28 Hz, 4H), 3.66-3.77 (m, 1H), 2.55-2.69 (m, 2H), 2.2-2.33 (m, 2H), 2.04-2.19 (m, 2H), 1.33-1.79 (m, 8H).

Workup

  1. customwas evaporated
  2. customdried in vacuo
  3. customThe residue was purified by prep

Sources & evidence

ORD record
ord-f63bdd238f0846d9ad1c7c14e9fb8613
Source dataset
uspto-grants-2014_09
Patent number
US08822510B2

Reaction notes

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