Ammonia → HCID 53851274, compound

HRID 1004620Notes

Reaction equation

HRID 1004620 reaction equation
N.[Na].[Si:3]([O:10][C@H:11]([C@H:14]1[C@@H:17]([C:18]#[CH:19])[N:16]([C@@H](C2C=CC=CC=2)C)[C:15]1=[O:28])[CH2:12][CH3:13])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].[Cl-].[NH4+]>CCOCC.C(O)C>[Si:3]([O:10][C@H:11]([C@H:14]1[C@@H:17]([C:18]#[CH:19])[NH:16][C:15]1=[O:28])[CH2:12][CH3:13])([C:6]([CH3:8])([CH3:7])[CH3:9])([CH3:5])[CH3:4]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 5360545Sodium2×HCID 53726250HCID 53726250, compound

Product 1

HCID 53851274HCID 53851274, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To 35 ml of ammonia were added sodium (50.4 mg, 2.19 mmol) and iron nitride nonahydrate (a catalytic amount) at -78° C. in an argon atmosphere. The mixture was stirred for 15 minutes, while the temperature was allowed to rise. Then, the temperature was returned to -78° C., followed by dropwise addition of a solution of the compound (509 mg, 1.37 mmol) prepared in Example 4 in ether (4 ml). After stirring at the same temperature for 40 minutes, sodium (189 mg, 8.20 mmol) was again added, and the mixture was stirred for a further 30 minutes at the same temperature. Next, ammonium chloride (3.5 g) and ethanol (3.5 ml) were added, followed by heating of the mixture. Ammonia was removed by evaporation, insoluble matters were removed by filtration, and the mixture was washed with ethyl acetate. The solvent was removed by evaporation under reduced pressure and the residue was purified by silica gel chromatography (hexane/ethyl acetate 4/1) to obtain 304 mg (yield 83%) of the title compound as a colorless crystals.

Workup

  1. customwas returned to -78° C.
  2. stirringAfter stirring at the same temperature for 40 minutes
  3. stirringthe mixture was stirred for a further 30 minutes at the same temperature
  4. temperatureby heating of the mixture
  5. customAmmonia was removed by evaporation, insoluble matters
  6. customwere removed by filtration
  7. washthe mixture was washed with ethyl acetate
  8. customThe solvent was removed by evaporation under reduced pressure
  9. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate 4/1)

Sources & evidence

ORD record
ord-a1c995010549450aa03b2f9a578cc0de
Source dataset
uspto-grants-2000_04
Patent number
US06051569

Reaction notes

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