Dimethylamine, hydrochloride → HCID 67279386, compound

HRID 751635Notes

Reaction equation

HRID 751635 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 (153 g, 187 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 stiffed 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. mr/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. customthe reaction stiffed 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-aa9e998721f64b3a9f63388056a5080d
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

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