Hydrochloric Acid → HCID 86722994, compound

HRID 1486201Notes

Reaction equation

HRID 1486201 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:21][CH2:22][S:23][CH3:24])[CH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][C:16]([O:18]CC)=[O:17])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO.C1COCC1>[C:1]([O:5][C:6]([N:8]([CH2:21][CH2:22][S:23][CH3:24])[CH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][C:16]([OH:18])=[O:17])[CH2:11][CH2:10]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86722995HCID 86722995, compound

Product 1

HCID 86722994HCID 86722994, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-[4-[tert-butoxycarbonyl(2-methylsulfanylethyl)amino]cyclohexyl]acetate (2.11 g, 5.89 mmol) in methanol (10 mL) and THF (10 mL) was added NaOH (10 mL, 1M aqueous). The resulting solution was stirred for 3.75 hours then acidified with HCl (2M, aqueous to pH 2). The mixture was extracted with ethyl acetate, washed with brine, dried over magnesium sulfate and concentrated. The residue was purified by silica chromatography (25 g silica; eluted with 20-60% ethyl acetate in hexanes) to give the title compound as a 6.9:1 mixture of trans to cis isomers.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica chromatography (25 g silica; eluted with 20-60% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-5dd2bdc8f5674f8590fb7f142d2bc7f8
Source dataset
uspto-grants-2016_08
Patent number
US09422314B2

Reaction notes

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