Ammonia → HCID 19757887, compound

HRID 1587545Notes

Reaction equation

HRID 1587545 reaction equation
[C:1]1([CH2:7][N:8](S(C2C=CC(C)=CC=2)(=O)=O)[CH2:9][CH2:10][CH2:11][N:12]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:13][CH2:14][CH2:15][N:16]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)S(C2C=CC(C)=CC=2)(=O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N.[Na].[Cl-].[NH4+]>>[C:1]1([CH2:7][NH:8][CH2:9][CH2:10][CH2:11][N:12]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:13][CH2:14][CH2:15][NH:16][CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 4

HCID 222Ammonia2×HCID 25517Ammonium ChlorideHCID 5360545Sodium2×HCID 19757880HCID 19757880, compound

Product 1

HCID 19757887HCID 19757887, compound

Procedure

Mix 1,9-bis[(phenyl)methyl]-1,9-bis[(4-methylphenyl)sulfonyl]-5-(t-butyloxycarbonyl)-1,5,9-triazanonane (720 mg, 1 mmol) in dry liquid ammonia (25 mL) at -40° C. Add small pieces of sodium until a permanent blue color remains. Discharge the excess sodium with saturated ammonium chloride. Allow the ammonia to evaporate spontaneously and partition the residue between ethyl acetate and water. Separate the organic phase, dry (MgSO4) and evaporate the solvent in vacuo. Purify by silica gel chromatography to give the title compound.

Workup

  1. customto evaporate spontaneously
  2. custompartition the residue between ethyl acetate and water
  3. customSeparate the organic phase
  4. dry with materialdry (MgSO4)
  5. customevaporate the solvent in vacuo
  6. customPurify by silica gel chromatography

Sources & evidence

ORD record
ord-b5f62e19776a4135bdad05d8ee8a6dfb
Source dataset
uspto-grants-1993_06
Patent number
US05217964

Reaction notes

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