Hydrochloric Acid → HCID 86722967, compound

HRID 1404363Notes

Reaction equation

HRID 1404363 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:21][CH2:22][N:23]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1)[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].CO.O.[OH-].[Li+].Cl>C1COCC1.O>[C:1]([O:5][C:6]([N:8]([CH2:21][CH2:22][N:23]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1)[CH:9]1[CH2:10][CH2:11][CH:12]([CH2:15][C:16]([OH:18])=[O:17])[CH2:13][CH2:14]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 86722968HCID 86722968, compound

Product 1

HCID 86722967HCID 86722967, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-[4-[tert-butoxycarbonyl-[2-[tert-butoxycarbonyl(2-pyridyl)amino]ethyl]amino]cyclohexyl]acetate (968 mg, 1.91 mmol) in THF (3 mL); methanol (3 mL) and water (6 mL) was added lithium hydroxide monohydrate (397 mg, 9.7 mmol). The resulting solution was stirred for 2.25 hr, then acidified to pH 3 with 1N HCl. The resulting mixture was extracted with dichloromethane (4 times). The combined organic extract was dried over magnesium sulfate and concentrated. The residue was purified by silica chromatography (10 g silica; eluted with 40-100% ethyl acetate in hexanes) to give the title compound as a 6:1 mixture of trans:cis isomers.

Workup

  1. extractionThe resulting mixture was extracted with dichloromethane (4 times)
  2. extractionThe combined organic extract
  3. dry with materialwas dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica chromatography (10 g silica; eluted with 40-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-30ae183c56a34504a9b34b539e3059aa
Source dataset
uspto-grants-2014_12
Patent number
US08912169B2

Reaction notes

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