Lithium hydroxide, monohydrate → [({5-[(1R)-1-(2-tert-butoxy-2-oxoethyl)-4-cyclohexylbutyl]-1,2,4-oxadiazol-3-yl}methyl)(methyl)amino]acetic acid

HRID 2084490Notes

Reaction equation

HRID 2084490 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:19]2[O:23][N:22]=[C:21]([CH2:24][N:25]([CH2:27][C:28]([O:30]CC)=[O:29])[CH3:26])[N:20]=2)[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O[Li].O>O1CCOCC1.O>[C:15]([O:14][C:12](=[O:13])[CH2:11][C@H:10]([C:19]1[O:23][N:22]=[C:21]([CH2:24][N:25]([CH2:27][C:28]([OH:30])=[O:29])[CH3:26])[N:20]=1)[CH2:9][CH2:8][CH2:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)([CH3:18])([CH3:16])[CH3:17]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 60077674tert-butyl(3R)-6-cyclohexyl-3-(3-{[(2-ethoxy-2-oxoethyl)(methyl)amino]methyl}-1,2,4-oxadiazol-5-yl)hexanoate

Product 1

HCID 60077601[({5-[(1R)-1-(2-tert-butoxy-2-oxoethyl)-4-cyclohexylbutyl]-1,2,4-oxadiazol-3-yl}methyl)(methyl)amino]acetic acidYield 120.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl (3R)-6-cyclohexyl-3-(3-([(2-ethoxy-2-oxoethyl)(methyl)amino]methyl}-1,2,4-oxadiazol-5-yl)hexanoate (preparation 132) (1.00 g, 2.21 mmol) in dioxan (20 ml) and H2O (20 ml) was treated with LiOH.H2O (193 mg, 2.21 mmol) and the reaction mixture stirred at room temperature for 19 hours. The solvent was removed under reduced pressure. The residue was dissolved in EtOAc and washed with brine. The aqueous was extracted with EtOAc (×3). The combined organic extracts were dried over anhydrous Na2SO4 and filtered. The solvent was removed under reduced pressure to afford the title compound as a white foam (1.13 g).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with brine
  4. extractionThe aqueous was extracted with EtOAc (×3)
  5. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2a6f5e8d08774121b50c15877372524d
Source dataset
uspto-grants-2004_04
Patent number
US06716861B2

Reaction notes

Loading…