Hydrochloric Acid → HCID 59201216, compound

HRID 1942305Notes

Reaction equation

HRID 1942305 reaction equation
[OH-].[Li+].C[O:4][C:5](=[O:36])[CH2:6][C@@H:7]1[CH2:12][CH2:11][N:10]([C@@H:13]([CH2:20][CH2:21][C:22]([F:25])([F:24])[F:23])[CH2:14][CH2:15][CH:16]([CH3:19])[CH2:17][OH:18])[C@H:9]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=2)[CH2:8]1.Cl.C([O-])(O)=O.[Na+]>O.C1COCC1>[OH:18][CH2:17][CH:16]([CH3:19])[CH2:15][CH2:14][C@@H:13]([N:10]1[CH2:11][CH2:12][C@@H:7]([CH2:6][C:5]([OH:36])=[O:4])[CH2:8][C@H:9]1[C:26]1[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:33])[F:34])=[CH:28][CH:27]=1)[CH2:20][CH2:21][C:22]([F:25])([F:24])[F:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 516892Sodium BicarbonateHCID 59201248HCID 59201248, compound

Product 1

HCID 59201216HCID 59201216, compoundYield 43.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide (26.2 mg, 1.095 mmol) in water (1.000 ml) was added to a stirred solution of methyl{(2S,4R)-1-[(1R,4R/S)-5-hydroxy-4-methyl-1-(3,3,3-trifluoropropyl)pentyl]-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetate (Example 32, Step 1, 109 mg, 0.219 mmol) in THF (2 ml) at RT. The mixture was stirred at RT o/n. 2N HCl (1 ml) was added The pH of the aqueous layer was adjusted to 7 with NaHCO3 (aq). The aqueous layer was extracted with DCM (×3). The combined extracts were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography (silica, 2-4-8% MeOH/DCM) to give the title compound (mixture of diastereomers, 46 mg) as a colourless foam. M/Z 484 (MH+).

Workup

  1. extractionThe aqueous layer was extracted with DCM (×3)
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by chromatography (silica, 2-4-8% MeOH/DCM)

Sources & evidence

ORD record
ord-b929ebd9400144f295108a0a72437414
Source dataset
uspto-grants-2013_03
Patent number
US08389547B2

Reaction notes

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