Hydrochloric Acid → (alphaS)-alpha-Aminocyclohexaneacetic acid

HRID 346705

Reaction equation

HRID 346705 reaction equation
Cl.CN(C(ON1N=N[C:12]2[CH:13]=[CH:14][CH:15]=[N:16][C:11]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:26](N(C(C)C)CC)(C)[CH3:27].[C:35](=[O:38])(O)[O-:36].[Na+]>CN(C=O)C>[CH2:15]1[CH2:14][CH2:13][CH:12]([C@H:11]([NH2:16])[C:35]([OH:36])=[O:38])[CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 736848(alphaS)-alpha-Aminocyclohexaneacetic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HCl (1.717 g, 6.87 mmol), HATU (2.618 g, 6.89 mmol) and diisopropylethyl amine (4.00 mL, 23.0 mmol) were added to a solution of the compound from Example 1, step 2 (1.704 g, 6.24 mmol) in anhydrous DMF (10 mL) at RT. The reaction was stirred at RT for 2.5 h. The reaction was diluted with saturated aqueous sodium bicarbonate (50 mL) and extracted with ether (150+100 mL). The organic phases were washed with water (100+50 mL), dried (MgSO4) and concentrated in vacuo to give 2.994 g of a yellow oil.

Workup

  1. extractionextracted with ether (150+100 mL)
  2. washThe organic phases were washed with water (100+50 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0b852f742e434fdf8128ea80219336fe
Source dataset
uspto-grants-2007_02
Patent number
US07173046B2

Linked notes

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