Hydrochloric Acid → HCID 16776699, compound

HRID 1191027Notes

Reaction equation

HRID 1191027 reaction equation
Cl.C(OC([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:13][CH:12]=1)=O)(C)(C)C>O1CCOCC1>[CH3:20][C:19]([CH3:22])([CH3:21])[C:18]([NH:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][NH2:9])=[CH:12][CH:13]=1)=[O:23]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 46915208HCID 46915208, compound

Product 1

HCID 16776699HCID 16776699, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Add 4M hydrogen chloride in dioxane (20 mL) to a solution of N-(tert-butoxycarbonyl)-4-(2,2-dimethyl-propionylamino)-benzylamine (2 g, 6.53 mmol) in anhydrous 1,4-dioxane (50 mL) at room temperature. Stir overnight and partition the reaction mixture between saturated aqueous NaHCO3 (200 mL) and DCM (500 mL). Extract the aqueous phase with DCM/iso-propanol (85:15, 2×100 mL) and then with DCM/iso-propanol (3:1, 2×100 mL). Dry the combined organic extracts over Na2SO4, filter and concentrate in vacuo. Purify by SCX chromatography eluting with DCM and DCM/2M ammonia in methanol (1:1) to obtain the title compound as a waxy colorless oil (1.13 g, 84%). MS (ES−) m/z: 205.1 (M−H)−.

Workup

  1. custompartition the reaction mixture between saturated aqueous NaHCO3 (200 mL) and DCM (500 mL)
  2. extractionExtract the aqueous phase with DCM/iso-propanol (85:15, 2×100 mL)
  3. dry with materialDry the combined organic extracts over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customPurify by SCX chromatography
  7. washeluting with DCM and DCM/2M ammonia in methanol (1:1)

Sources & evidence

ORD record
ord-ee95ba0fe9e94d08ae8b62f487a25e32
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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