Ammonia → HCID 19757892, compound

HRID 1587550Notes

Reaction equation

HRID 1587550 reaction equation
[C:1]1([N:7](S(C2C=CC(C)=CC=2)(=O)=O)[CH2:8][CH2:9][CH2:10][N:11]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:12][CH2:13][CH2:14][N:15]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=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([NH:7][CH2:8][CH2:9][CH2:10][N:11]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:12][CH2:13][CH2:14][NH:15][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 4

HCID 222Ammonia2×HCID 25517Ammonium ChlorideHCID 5360545Sodium2×HCID 19757881HCID 19757881, compound

Product 1

HCID 19757892HCID 19757892, compound

Procedure

Mix 1,9-bis[(phenyl)]-1,9-bis[(4-methylphenyl)sulfonyl]-5-(t-butyloxycarbonyl)-1,5,9-triazanonane (691 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-9eca5d7848514889813f61c7083c6e51
Source dataset
uspto-grants-1993_06
Patent number
US05217964

Reaction notes

Loading…