Triethylamine → HCID 178485750, compound

HRID 1031751Notes

Reaction equation

HRID 1031751 reaction equation
Cl.C[N:3]([CH3:15])[C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6].[C:16]([O:20][C:21]([NH:23][CH2:24][C@H:25]1[CH2:30][CH2:29][C@H:28]([C:31](O)=[O:32])[CH2:27][CH2:26]1)=[O:22])([CH3:19])([CH3:18])[CH3:17].C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C>ClCCl.O>[CH3:15][NH:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[NH:6][C:31]([C@H:28]1[CH2:27][CH2:26][C@H:25]([CH2:24][NH:23][C:21]([O:20][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:22])[CH2:30][CH2:29]1)=[O:32]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12653778(2S)-2-Amino-N,N-dimethyl-3-phenylpropanamide hydrochlorideHCID 178453624HCID 178453624, compound

Product 1

HCID 178485750HCID 178485750, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To the compound (I) (19.00 g), 4 N hydrogen chloride/1,4-dioxane solution (325 ml) was added under room temperature, and the mixture was stirred at the same temperature for 30 minutes. The mixture was concentrated under a reduced pressure, and L-phenylalanine dimethylamide hydrochloride (II) was obtained quantitatively as a white powder. Subsequently, to a solution of the compound (II), trans-4-(t-butoxycarbonylaminomethyl)cyclohexylcarboxylic acid (16.70 g) and triethylamine (9.75 ml) in dry dichloromethane (200 ml), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (13.69 g) was added under ice-cooling, the mixture was stirred for 2 hours, and again stirred at room temperature for 2 hours. To the reaction water was added to obtain an organic layer, which was washed with 10% aqueous citric acid, water, 5% aqueous sodium hydrogen carbonate, and water, in this order, followed by drying over anhydrous sodium sulfate. The solids were filtered off, the filtrate concentrated under a reduced pressure and the residue was washed with diethyl ether, followed by filtration to give N-[trans-4-(t-butoxycarbonylaminomethyl)cyclohexylcarbonyl]-L-phenylalanine dimethylamide (III) (21.90 g). The structure was confirmed by NMR.

Workup

  1. temperaturecooling
  2. stirringagain stirred at room temperature for 2 hours
  3. additionwas added
  4. customto obtain an organic layer, which
  5. washwas washed with 10% aqueous citric acid, water, 5% aqueous sodium hydrogen carbonate, and water, in this order
  6. dry with materialby drying over anhydrous sodium sulfate
  7. filtrationThe solids were filtered off
  8. concentrationthe filtrate concentrated under a reduced pressure
  9. washthe residue was washed with diethyl ether
  10. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-5c76521bd4934048885bf7a4b2e7e588
Source dataset
uspto-grants-1990_09
Patent number
US04954512

Reaction notes

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