Hexamethyldisilazane → HCID 19775184, compound

HRID 1613130Notes

Reaction equation

HRID 1613130 reaction equation
Cl.[C:2]([CH2:5][CH:6]([OH:23])[CH2:7][NH:8][CH:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][C:13]([O:21][CH3:22])=[C:14]([O:19][CH3:20])[CH:15]=2)[CH2:10]1)(O)=[O:3].C[Si](N[Si](C)(C)C)(C)C>C1(C)C(C)=CC=CC=1>[CH3:20][O:19][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][C:13]=1[O:21][CH3:22])[CH2:10][CH:9]([N:8]1[CH2:7][CH:6]([OH:23])[CH2:5][C:2]1=[O:3])[CH2:18][CH2:17]2

Participants

4

Reactant 2

HCID 13838HexamethyldisilazaneHCID 131717800HCID 131717800, compound

Product 1

HCID 19775184HCID 19775184, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To N-(3-carboxy-2-hydroxypropyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-napthylamine hydrocloride (ST 576, prepared as described in the Italian patent application 47652A/88) (1 g, 2.89 mmoles) in xylene (40 mL), 1.2 mL HMDS and TMSCI (few drops) were added. The resulting mixture was refluxed under stirring for 24 hours. Xylene was evaporated, the residue was taken up with EtOH (40 mL) and 1N HCl in isopropanol (1 mL) was added thereto. After 5 minutes, NaHCO3 was added till neutrality, the mixture was filtered and the filtrate evaporated. The residue was chromatographed on silica gel using EtOAc--MeOH (95:5) as eluant. 600 mg of the title compound were obtained. Yield 71%.

Workup

  1. temperatureThe resulting mixture was refluxed
  2. customXylene was evaporated
  3. additionwas added
  4. waitAfter 5 minutes
  5. additionNaHCO3 was added till neutrality, the mixture
  6. filtrationwas filtered
  7. customthe filtrate evaporated
  8. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-c7f63870aaaf40eca9384377cc7a9a42
Source dataset
uspto-grants-1993_03
Patent number
US05192759

Reaction notes

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