Dimethylamine → HCID 15130877, compound

HRID 1870304Notes

Reaction equation

HRID 1870304 reaction equation
[C:1]([NH:11][C@H:12]([C:16]([OH:18])=O)[CH:13]([CH3:15])[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C1N=[CH:22][N:21](C(N2C=NC=C2)=O)[CH:20]=1.CNC>CN(C=O)C.C1COCC1.C(OCC)(=O)C>[CH3:20][N:21]([CH3:22])[C:16](=[O:18])[C@H:12]([CH:13]([CH3:15])[CH3:14])[NH:11][C:1]([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

7

Reactant 3

HCID 674DimethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 726987N-Carbobenzoxy-L-valine

Product 1

HCID 15130877HCID 15130877, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2.51 g (10 mmol) of Cbz-L-Valine (Bachem) in 20 mL of DMF was added 1.46 g (9 mmol) of CDI and the mixture was stirred for 50 min. To this mixture was added 6 mL (12 mmol) of dimethylamine (Aldrich) in 5 mL of THF and the reaction mixture was stirred for 18 hours. The mixture was taken up in 100 mL of ethyl acetate, washed with 10% HCl (3×40 mL), 10 mL of brine, and 20% potassium carbonate (2×50 mL), and dried over MgSO4. The mixture was filtered and concentrated to yield Cbz-L-valine N,N-dimethyl amide, which was hydrogenated under standard conditions with 10% Pd/C as the catalyst to remove the Cbz group and provide the title compound as an oil.

Workup

  1. stirringthe reaction mixture was stirred for 18 hours
  2. washwashed with 10% HCl (3×40 mL), 10 mL of brine, and 20% potassium carbonate (2×50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationThe mixture was filtered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4907240ee5b94e50a5e7baa056991cc6
Source dataset
uspto-grants-2000_08
Patent number
US06096782

Reaction notes

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