Hydrochloric Acid → HCID 86722967, compound

HRID 1486176Notes

Reaction equation

HRID 1486176 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 1 N 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-0084f3c88ddc4ad1a459cae75c11c76f
Source dataset
uspto-grants-2016_08
Patent number
US09422314B2

Reaction notes

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