Hydrochloric Acid → HCID 30046248, compound

HRID 1191030Notes

Reaction equation

HRID 1191030 reaction equation
Cl.C(OC([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([C@@H:20]2[CH2:22][C@H:21]2[CH3:23])=[O:19])=[CH:13][CH:12]=1)=O)(C)(C)C.C(OCC)C>O1CCOCC1>[CH3:23][C@@H:21]1[CH2:22][C@H: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 AcidHCID 3283Diethyl EtherHCID 59828913HCID 59828913, compound

Product 1

HCID 30046248HCID 30046248, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Add 4M hydrogen chloride in dioxane (17.7 mL) to a solution of (±)-trans-N-(tert-butoxycarbonyl)-4-[(2-methyl-cyclopropanecarbonyl)-amino]-benzylamine (1.72 g, 5.65 mmol) in dioxane (35.4 mL). Stir at room temperature overnight, add diethyl ether and concentrate in vacuo several times. Partition the residue between saturated aqueous NaHCO3 (200 mL) and DCM (500 mL). Extract the aqueous phase with DCM/iso-propanol (3:1, 4×200 mL). Dry the combined organic extracts over Na2SO4, filter and concentrate in vacuo. Load the compound into a SCX column (10 g), wash the column with DCM (100 mL), and then elute with 2M ammonia in methanol/DCM (1:1, 100 mL) to afford the title compound (0.935 g, 81%) as a waxy colorless oil.

Workup

  1. concentrationconcentrate in vacuo several times
  2. customPartition the residue between saturated aqueous NaHCO3 (200 mL) and DCM (500 mL)
  3. extractionExtract the aqueous phase with DCM/iso-propanol (3:1, 4×200 mL)
  4. dry with materialDry the combined organic extracts over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. washLoad the compound into a SCX column (10 g), wash the column with DCM (100 mL)
  8. washelute with 2M ammonia in methanol/DCM (1:1, 100 mL)

Sources & evidence

ORD record
ord-1238b15df3e6477a93a568fec91ad51b
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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