Hydrochloric Acid → HCID 178453517, compound

HRID 1404379Notes

Reaction equation

HRID 1404379 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:21][CH2:22][CH2:23][NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[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.CC(N)C1C=CC=CC=1>CO.C1COCC1>[C:1]([O:5][C:6]([N:8]([CH2:21][CH2:22][CH2:23][NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@H:9]1[CH2:14][CH2:13][C@H:12]([CH2:15][C:16]([OH:18])=[O:17])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 74081-PhenethylamineHCID 14798Sodium HydroxideHCID 86722986HCID 86722986, compound

Product 1

HCID 178453517HCID 178453517, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-[4-[tert-butoxycarbonyl-[3-(tert-butoxycarbonylamino)propyl]amino]cyclohexyl]acetate (1.53 g, 3.47 mmol) in methanol (3 mL) and THF (3 mL) was added NaOH (7.5 mL, 1M aqueous). The resulting solution was stirred for 2.75 hours the acidified with HCl (8 mL, 1M aqueous). This mixture was extracted with ethyl acetate, washed with brine dried over magnesium sulfate and concentrated. The residue was taken up in ether (5 mL). To this solution was added (−) α-methyl-benzylamine (428 μL, 347 mmol) and the resulting solution allowed to stand overnight. The crystalline mass was filtered, washed with ether and the collected solid recrystallized from isopropanol/ether to give 1.1 g of solid. The material was suspended in ethyl acetate, washed with 1M HCl aqueous, followed by brine, dried over magnesium sulfate and concentrated to give the title compound.

Workup

  1. extractionThis mixture was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. waitto stand overnight
  6. filtrationThe crystalline mass was filtered
  7. washwashed with ether
  8. customthe collected solid recrystallized from isopropanol/ether

Sources & evidence

ORD record
ord-65fecaa0194b4e3ba21a67e45829e867
Source dataset
uspto-grants-2014_12
Patent number
US08912169B2

Reaction notes

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