Triethylamine → N,N'-bis[(1S)-(2-naphthyl)-2-hydroxy-2-methylpropyl]-2,2-dimethylpropane-1,3-diamide

HRID 1182405Notes

Reaction equation

HRID 1182405 reaction equation
[NH2:1][C@@H:2]([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1)[C:3]([CH3:6])([OH:5])[CH3:4].C([N:19]([CH2:22][CH3:23])CC)C.[CH3:24][C:25]([CH3:32])([C:29](Cl)=[O:30])[C:26](Cl)=[O:27].[Cl-].[NH4+]>ClCCl>[CH:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[CH:16][C:7]=1[C@H:2]([NH:1][C:26](=[O:27])[C:25]([CH3:32])([CH3:24])[C:29]([NH:19][C@@H:22]([C:23]1[CH:7]=[CH:8][C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=1)[C:3]([CH3:2])([OH:5])[CH3:4])=[O:30])[C:3]([OH:5])([CH3:6])[CH3:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 4523180Dimethylmalonyl DichlorideHCID 66807919(S)-1-amino-1-(2-naphthyl)-2-methyl-2-propanol

Product 1

HCID 66807932N,N'-bis[(1S)-(2-naphthyl)-2-hydroxy-2-methylpropyl]-2,2-dimethylpropane-1,3-diamideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

Under a nitrogen atmosphere, 1.5 g of (S)-1-amino-1-(2-naphthyl)-2-methyl-2-propanol, 0.84 g of triethylamine (dehydrated), and 13 mL of dichloromethane (dehydrated) were mixed and then cooled to an inner temperature of −10° C. 0.6 g of dimethylmalonic acid dichloride was added dropwise thereto over 3 minutes. The resulting mixture was warmed to room temperature. The mixture was stirred as such for 7 hours to effect reaction. After completion of the reaction, 20 mL of an aqueous saturated ammonium chloride solution was added thereto to separate into layers. The organic layer obtained was washed three times with 25 mL of water and concentrated. The concentrated residue was dried under reduced pressure at an inner temperature of 40° C. to obtain 1.8 g of N,N′-bis[(1S)-(2-naphthyl)-2-hydroxy-2-methylpropyl]-2,2-dimethylpropane-1,3-diamide (yield: 100%).

Workup

  1. temperatureThe resulting mixture was warmed to room temperature
  2. customreaction
  3. additionwas added
  4. customto separate into layers
  5. customThe organic layer obtained
  6. washwas washed three times with 25 mL of water
  7. concentrationconcentrated
  8. customThe concentrated residue was dried under reduced pressure at an inner temperature of 40° C.

Sources & evidence

ORD record
ord-3c8cdc2353ad4d05872d5ded6fce08de
Source dataset
uspto-grants-2007_10
Patent number
US07288674B2

Reaction notes

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