Lithium hydroxide, monohydrate → ((S)-1-{hydroxy-[5-(4-trifluoromethoxy-phenyl)-1,3,4-oxadiazol-2-yl]-methyl}-propyl)-carbamic acid tert-butyl ester

HRID 1455587Notes

Reaction equation

HRID 1455587 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:31][CH3:32])[C@H:10]([O:27]C(=O)C)[C:11]1[O:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=2)=[N:14][N:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+]>C1COCC1.O>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([CH:10]([OH:27])[C:11]1[O:12][C:13]([C:16]2[CH:17]=[CH:18][C:19]([O:22][C:23]([F:25])([F:24])[F:26])=[CH:20][CH:21]=2)=[N:14][N:15]=1)[CH2:31][CH3:32])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86607345Acetic acid (S)-2-tert-butoxycarbonylamino-1-[5-(4-trifluoromethoxy-phenyl)-1,3,4-oxadiazol-2-yl]-butyl ester

Product 1

HCID 57535328((S)-1-{hydroxy-[5-(4-trifluoromethoxy-phenyl)-1,3,4-oxadiazol-2-yl]-methyl}-propyl)-carbamic acid tert-butyl esterYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Acetic acid (S)-2-tert-butoxycarbonylamino-1-[5-(4-trifluoromethoxy-phenyl)-1,3,4-oxadiazol-2-yl]-butyl ester (0.61 mmol, 0.28 g) is dissolved in a mixture of THF (10 mL) and water (10 mL). Lithium hydroxide hydrate (1.22 mmol, 0.051 g) is added and the reaction mixture stirred for 2 h. The solvents are evaporated under reduced pressure and the residue transferred into a separating funnel with 300 mL ethyl acetate and 50 mL water. The phases are separated and the organic phase washed with brine (100 mL). The organic phase is then dried with magnesium sulfate. The solvent is evaporated under reduced pressure and dried under high vacuum to yield ((S)-1-{hydroxy-[5-(4-trifluoromethoxy-phenyl)-1,3,4-oxadiazol-2-yl]-methyl}-propyl)-carbamic acid tert-butyl ester as an oil (0.225 g, 89%) MS: m/z=440 (M+Na+), 418 (M+H+)

Workup

  1. customThe solvents are evaporated under reduced pressure
  2. customthe residue transferred into a separating funnel with 300 mL ethyl acetate and 50 mL water
  3. customThe phases are separated
  4. washthe organic phase washed with brine (100 mL)
  5. dry with materialThe organic phase is then dried with magnesium sulfate
  6. customThe solvent is evaporated under reduced pressure
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-bd839e88f3e74b23915738673ed545fa
Source dataset
uspto-grants-2009_01
Patent number
US07482448B2

Reaction notes

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