Diethyl Ether → HCID 56644161, compound

HRID 71268Notes

Reaction equation

HRID 71268 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:14][O:15][CH2:16][C:17]3[O:21][N:20]=[C:19]([C:22]4[CH:39]=[CH:38][C:25]([CH2:26][N:27]5[CH2:30][CH:29]([C:31]([O:33]C(C)(C)C)=[O:32])[CH2:28]5)=[CH:24][CH:23]=4)[N:18]=3)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.CCOCC>FC(F)(F)C(O)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:14][O:15][CH2:16][C:17]3[O:21][N:20]=[C:19]([C:22]4[CH:23]=[CH:24][C:25]([CH2:26][N:27]5[CH2:30][CH:29]([C:31]([OH:33])=[O:32])[CH2:28]5)=[CH:38][CH:39]=4)[N:18]=3)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 66692288Tert-butyl 1-(4-(5-(((1-(4-fluorophenyl)cyclohexyl)methoxy)methyl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylate

Product 1

HCID 56644161HCID 56644161, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl 1-(4-(5-(((1-(4-fluorophenyl)cyclohexyl)methoxy)methyl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylate (37 mg, 69 mol) in trifluoroacetic acid (1.5 mL) was stirred at room temperature for 2 h. Trifluoroacetic acid was removed under reduced pressure, followed by co-evaporation with ether to obtain a solid which was stirred with ether (7 mL) for 3.5 h, filtered and dried to obtain 1-(4-(5-(((1-(4-fluorophenyl)cyclohexyl)methoxy)methyl)-1,2,4-oxadiazol-3-yl)benzyl) azetidine-3-carboxylic acid (26 mg, 63% yield) as a white solid. LC/MS: m/e 480.21 (M+H)+. 1H NMR (400 MHz, CD3OD): δ ppm 8.17 (d, J=8.03 Hz, 2H), 7.65 (d, J=7.78 Hz, 2H), 7.43 (dd, J=8.28, 5.52 Hz, 2H), 7.02 (t, J=8.53 Hz, 2H), 4.68 (s, 2H), 4.52 (s, 2H), 4.38 (d, J=7.53 Hz, 4H), 3.72 (ddd, J=16.63, 8.78, 8.47 Hz, 1H), 3.59 (s, 2H), 2.05-2.30 (m, 2H), 1.68-1.88 (m, 2H), 1.48-1.69 (m, 3H), 1.27-1.47 (m, 3H).

Workup

  1. customTrifluoroacetic acid was removed under reduced pressure
  2. customto obtain a solid which
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-10790e468e3b4b45bce13bdf9b46a764
Source dataset
uspto-grants-2014_09
Patent number
US08822510B2

Reaction notes

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