Dimethylamine → HCID 118177262, compound

HRID 1485090Notes

Reaction equation

HRID 1485090 reaction equation
CC1C=CC(S(O[CH2:12][C@@H:13]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][C:15]#[N:16])(=O)=O)=CC=1.[CH3:25][NH:26][CH3:27].C(N(CC)CC)C>C(O)C>[C:15]([CH2:14][C@H:13]([NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:12][N:26]([CH3:27])[CH3:25])#[N:16]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 8471TriethylamineHCID 118113164HCID 118113164, compound

Product 1

HCID 118177262HCID 118177262, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution in ethanol (20 mL) of the compound (1.32 g) obtained in step (1) above, dimethylamine (about 50%, aqueous solution, 3.92 mL) and triethylamine (519 μL) were added and the mixture was stirred at 80° C. for an hour. After being cooled to room temperature, the reaction mixture was concentrated under reduced pressure. To the resulting residue, a saturated aqueous solution of sodium hydrogencarbonate was added and extraction was conducted with ethyl acetate. The combined organic layers were washed with saturated brine and after passage through a phase separator, they were concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=99:1-95:5) to give tert-butyl [(2S)-1-cyano-3-(dimethylamino)propan-2-yl]carbamate as a pale yellow oil (340 mg).

Workup

  1. temperatureAfter being cooled to room temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionTo the resulting residue, a saturated aqueous solution of sodium hydrogencarbonate was added
  4. extractionextraction
  5. washThe combined organic layers were washed with saturated brine
  6. concentrationafter passage through a phase separator, they were concentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol=99:1-95:5)

Sources & evidence

ORD record
ord-a2bd23929ae0435ead184b481f3f209a
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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