Trifluoroacetic acid → N-(3-Azetidinyl)-5-{(1R)-4-cyclohexyl-1-[2-(hydroxyamino)-2-oxoethyl]butyl}-1,2,4-oxadiazole-3-carboxamide

HRID 2182940Notes

Reaction equation

HRID 2182940 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:16]2[O:20][N:19]=[C:18]([C:21]([NH:23][CH:24]3[CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25]3)=[O:22])[N:17]=2)[CH2:11][C:12]([NH:14][OH:15])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[NH:26]1[CH2:25][CH:24]([NH:23][C:21]([C:18]2[N:17]=[C:16]([C@@H:10]([CH2:11][C:12]([NH:14][OH:15])=[O:13])[CH2:9][CH2:8][CH2:7][CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[O:20][N:19]=2)=[O:22])[CH2:27]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59909842tert-Butyl 3-{[(5-{(1R)-4-cyclohexyl-1-[2-(hydroxyamino)-2-oxoethyl]butyl}-1,2,4-oxadiazol-3-yl)carbonyl]amino}-1-azetidinecarboxylate

Product 1

HCID 10134324N-(3-Azetidinyl)-5-{(1R)-4-cyclohexyl-1-[2-(hydroxyamino)-2-oxoethyl]butyl}-1,2,4-oxadiazole-3-carboxamideYield 98.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of tert-butyl 3-{[(5-{(1R)-4-cyclohexyl-1-[2-(hydroxyamino)-2-oxoethyl]butyl}-1,2,4-oxadiazol-3-yl)carbonyl]amino}-1-azetidinecarboxylate (Example 43) (160 mg, 0.33 mmol) in dichloromethane (10 ml) was cooled to 0° C. and treated with trifluoroacetic acid (7 ml) and the resulting mixture was stirred at 0° C. under a nitrogen atmosphere for 45 minutes. The solvent was removed under reduced pressure and the residue azeotroped from dichloromethane (×2). The residue was triturated with diethylether, filtered and dried to afford the title compound as a white solid (123 mg).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue azeotroped from dichloromethane (×2)
  3. customThe residue was triturated with diethylether
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-c7afa6ccb84e445eb80db0ad54fc78a5
Source dataset
uspto-grants-2005_05
Patent number
US06897306B2

Reaction notes

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