Trifluoroacetic acid → (3R)-3-{3-[(2-amino-2-oxoethoxy)methyl]-1,2,4-oxadiazol-5-yl}6-cyclohexylhexanoic acid

HRID 2183051Notes

Reaction equation

HRID 2183051 reaction equation
[NH2:1][C:2](=[O:29])[CH2:3][O:4][CH2:5][C:6]1[N:10]=[C:9]([C@H:11]([CH2:20][CH2:21][CH2:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[CH2:12][C:13]([O:15]C(C)(C)C)=[O:14])[O:8][N:7]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:1][C:2](=[O:29])[CH2:3][O:4][CH2:5][C:6]1[N:10]=[C:9]([C@H:11]([CH2:20][CH2:21][CH2:22][CH:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[CH2:12][C:13]([OH:15])=[O:14])[O:8][N:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59909799tert-Butyl (3R)-3-{3-[(2-amino-2-oxoethoxy)methyl]-1,2,4-oxadiazol-5-yl}-6-cyclohexylhexanoate

Product 1

HCID 59909790(3R)-3-{3-[(2-amino-2-oxoethoxy)methyl]-1,2,4-oxadiazol-5-yl}6-cyclohexylhexanoic acidYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl (3R)-3-{3-[(2-amino-2-oxoethoxy)methyl]-1,2,4-oxadiazol-5-yl}-6-cyclohexylhexanoate (Preparation 90) (280 mg, 0.86 mmol) in dichloromethane (7 ml) was treated with trifluoroacetic acid (3 ml) and stirred at room temperature for 4 hours. The solvent was removed under reduced pressure and the residue azeotroped from toluene and dichloromethane. The oil was purified by column chromatography on silica gel eluting with a gradient system of 100:0:0 (dichloromethane:methanol:acetic acid) gradually changing to 90:10:1 (dichloromethane:methanol:acetic acid) to afford a colourless oil which was triturated with diethyl ether and filtered to afford the title compound (155 mg).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue azeotroped from toluene and dichloromethane
  3. customThe oil was purified by column chromatography on silica gel eluting with a gradient system of 100:0:0 (dichloromethane:methanol:acetic acid)
  4. customto afford a colourless oil which
  5. customwas triturated with diethyl ether
  6. filtrationfiltered

Sources & evidence

ORD record
ord-423d3b810eb440a9ae14b1c2a2e97ab4
Source dataset
uspto-grants-2005_05
Patent number
US06897306B2

Reaction notes

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