Hydrochloric Acid → HCID 58495458, compound

HRID 1191029Notes

Reaction equation

HRID 1191029 reaction equation
Cl.C(OC([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([CH:20]2[C:22]([CH3:24])([CH3:23])[C:21]2([CH3:26])[CH3:25])=[O:19])=[CH:13][CH:12]=1)=O)(C)(C)C.C(Cl)Cl>O1CCOCC1>[CH3:25][C:21]1([CH3:26])[C:22]([CH3:23])([CH3:24])[CH:20]1[C:18]([NH:17][C:14]1[CH:13]=[CH:12][C:11]([CH2:10][NH2:9])=[CH:16][CH:15]=1)=[O:19]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 6344DichloromethaneHCID 58495597HCID 58495597, compound

Product 1

HCID 58495458HCID 58495458, compoundYield 107.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent4×

Procedure

Add 4M hydrogen chloride in dioxane (6.1 mL) to a solution of N-(tert-butoxycarbonyl)-4-[(2,2,3,3-tetramethyl-cyclopropanecarbonyl)-amino]-benzylamine (0.678 g, 1.958 mmol) in anhydrous 1,4-dioxane (12.2 mL) at room temperature. After stirring at room temperature for 3 h, the reaction is a solid mass. Add more 1,4-dioxane (12.2 mL), DCM (24.4 mL) and more 4M hydrogen chloride in dioxane (6.1 mL), and stir overnight. Concentrate in vacuo and partition the residue between saturated aqueous NaHCO3 (200 mL) and DCM (500 mL). Dry the organic phase over Na2SO4, filter and concentrate in vacuo. The aqueous phase was extracted with DCM/iso-propanol (3:1, 4×200 mL). Dry the combined organic extracts over Na2SO4, filter, combine with the organic fraction isolated above and concentrate in vacuo. Purify by SCX chromatography eluting with DCM and DCM/2M ammonia in methanol (1:1) to obtain the title compound (0.519 g, 100%). MS (ES+) m/z: 247.2 (M+H)+.

Workup

  1. stirringstir overnight
  2. concentrationConcentrate in vacuo
  3. custompartition the residue between saturated aqueous NaHCO3 (200 mL) and DCM (500 mL)
  4. dry with materialDry the organic phase over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. extractionThe aqueous phase was extracted with DCM/iso-propanol (3:1, 4×200 mL)
  8. dry with materialDry the combined organic extracts over Na2SO4
  9. filtrationfilter
  10. customisolated above
  11. concentrationconcentrate in vacuo
  12. customPurify by SCX chromatography
  13. washeluting with DCM and DCM/2M ammonia in methanol (1:1)

Sources & evidence

ORD record
ord-287c2a9e234f4ca080e03cf1bdf8352b
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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