Dimethylamine → HCID 59846251, compound

HRID 1697060Notes

Reaction equation

HRID 1697060 reaction equation
C1C=CC2N(O)N=NC=2C=1.C[CH2:12][N:13]=[C:14]=NCCCN(C)C.[CH2:22]([O:29][C:30]([NH:32][C:33]([CH3:39])([CH3:38])[CH2:34][C:35](O)=[O:36])=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.N(C)C>C(Cl)Cl>[CH2:22]([O:29][C:30](=[O:31])[NH:32][C:33]([CH3:39])([CH3:38])[CH2:34][C:35](=[O:36])[N:13]([CH3:14])[CH3:12])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 145510073-(((Benzyloxy)carbonyl)amino)-3-methylbutanoic acid

Product 1

HCID 59846251HCID 59846251, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

HOBt (1.242 g, 9.193 mmol) and EDCI (2.35 g, 12.26 mmol) were added to a solution of 3-benzyloxycarbonylamino-3-methyl-butyric acid (1.54 g, 6.129 mmol) in DCM (45 mL) at 0° C. The resulting mixture was stirred at 0° C. for 30 min, and a solution of Me2NH (2 M in THF, 12.26 mL, 24.51 mmol) was added. The reaction mixture was warmed up to RT and stirred overnight. The solvent was evaporated under reduced pressure, and the residue partitioned between EtOAc and a mixture of water, brine and NaHCO3 (sat aq). The organic layer was separated, washed with HCl (1 M), dried over anhydrous MgSO4, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (EtOAc/hexane) to afford (2-dimethylcarbamoyl-1,1-dimethyl-ethyl)-carbamic acid benzyl ester (1.14 g, 67% yield).

Workup

  1. temperatureThe reaction mixture was warmed up to RT
  2. stirringstirred overnight
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue partitioned between EtOAc
  5. additiona mixture of water, brine and NaHCO3 (sat aq)
  6. customThe organic layer was separated
  7. washwashed with HCl (1 M)
  8. dry with materialdried over anhydrous MgSO4
  9. filtrationfiltered
  10. customevaporated under reduced pressure
  11. customThe crude residue was purified by flash chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-b42369d28866459fb818896da09784fe
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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