Dimethylamine, hydrochloride → HCID 67279386, compound

HRID 1693380Notes

Reaction equation

HRID 1693380 reaction equation
[ClH:1].CNC.CCN(C(C)C)C(C)C.C(OC([NH:21][C@@H:22]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1)[C:23]([OH:25])=O)=O)(C)(C)C.CN(C(O[N:41]1[N:49]=[N:48][C:43]2C=CC=C[C:42]1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[ClH:1].[NH2:21][C@@H:22]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1)[C:23]([N:49]([NH:41][CH3:42])[NH:48][CH3:43])=[O:25]

Participants

6

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2734482Boc-3-(2-pyridyl)-Ala-OH

Product 1

HCID 67279386HCID 67279386, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of dimethylamine hydrochloride (0.153 g, 1.87 mmol) in DMF (8 mL) was added DIPEA (2 mL, 6.55 mmol), (S)-2-tert-butoxycarbonylamino-3-pyridin-2-ylpropionic acid (0.50 g, 1.87 mmol, Acros) and TBTU (0.60 g, 1.87 mmol). The reaction mixture was stirred at rt for 16 h. The solvent was removed in vacuo and the residue was dissolved in methanol (15 mL). To this was added 4M hydrochloric acid in dioxane (20 mL) and the reaction stirred at rt for 16 h. The solvent was removed in vacuo and the residue partitioned between water (100 mL) and ethyl acetate (2×100 mL). The aqueous layer was evaporated to dryness to give a solid, which was recrystallised from ethanol to give the title compound as a pale brown solid. m/z (ES+)=194.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in methanol (15 mL)
  3. additionTo this was added 4M hydrochloric acid in dioxane (20 mL)
  4. stirringthe reaction stirred at rt for 16 h
  5. customThe solvent was removed in vacuo
  6. customthe residue partitioned between water (100 mL) and ethyl acetate (2×100 mL)
  7. customThe aqueous layer was evaporated to dryness
  8. customto give a solid, which
  9. customwas recrystallised from ethanol

Sources & evidence

ORD record
ord-27d1789bfa9e44b8bd42cdc3faea09f5
Source dataset
uspto-grants-2012_04
Patent number
US08158622B2

Reaction notes

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