Water → HCID 23302088, compound

HRID 1952980Notes

Reaction equation

HRID 1952980 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][CH2:11][CH2:12][CH2:13][N:14]([CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][N:23]([CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:24][CH2:25][CH2:26][NH:27][C:28]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[C:1]1([CH2:7][CH2:8][NH:10][CH2:11][CH2:12][CH2:13][N:14]([CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][N:23]([CH2:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH2:24][CH2:25][CH2:26][NH:27][CH2:28][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 23302083HCID 23302083, compound

Product 1

HCID 23302088HCID 23302088, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Add a solution of 1,18-bis[[(phenyl)methyl]carbonyl]-5,14-bis-[(phenyl)methyl]-1,5,14,18-tetraazaoctadecane (3 g) in tetrahydrofuran (150 mL) dropwise to a suspension of lithium aluminum hydride (0.5 g) in tetrahydrofuran (500 mL). Stir the reaction for 48 hours at room temperature. Decompose the excess reducing agent by dropwise addition of water (1 mL), 15% sodium hydroxide (1 mL) and water (3 mL). Filter the mixture and concentrate the filtrate under vacuum. Dissolve the residue in ethanol (100 mL) and add anhydrous hydrogen chloride gas to provide the tetrahydrochloride salt of 1,18-bis[(2-phenyl)ethyl]-5,14-bis-[(phenyl)methyl]-1,5,14,18-tetraazaoctadecane. Scheme D, step C: Hydrogenate this product in ethanol (150 mL) in the presence of Pearlman's catalyst (0.3 g) at 43 psig on a Parr hydrogenation apparatus for 24 hours. Filter the reaction and concentrate the filtrate under vacuum. Crystallize the residue from 2-propanol to provide the title compound as a hemihydrate, mp 322-324° C. (dec.).

Workup

  1. customthe reaction for 48 hours at room temperature
  2. filtrationFilter the mixture
  3. concentrationconcentrate the filtrate under vacuum
  4. dissolutionDissolve the residue in ethanol (100 mL)
  5. additionadd anhydrous hydrogen chloride gas

Sources & evidence

ORD record
ord-d298ac8f88ab402ba4d7b7cf37ff6938
Source dataset
uspto-grants-2000_09
Patent number
US06114394

Reaction notes

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