Chloroform → HCID 22999774, compound

HRID 397300Notes

Reaction equation

HRID 397300 reaction equation
[Si:1]([C:8]1[N:9]([S:17]([N:20]([CH3:22])[CH3:21])(=[O:19])=[O:18])[C:10]([CH:13]=[CH:14][C:15]#[N:16])=[CH:11][N:12]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(Cl)(Cl)Cl>C(O)C.C1COCC1.[Pt]=O>[Si:1]([C:8]1[N:9]([S:17]([N:20]([CH3:22])[CH3:21])(=[O:19])=[O:18])[C:10]([CH2:13][CH2:14][CH2:15][NH2:16])=[CH:11][N:12]=1)([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 6212ChloroformHCID 54107123HCID 54107123, compound

Product 1

HCID 22999774HCID 22999774, compound

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 29 (2.1 mmol) is dissolved in absolute ethanol (75 mL) and THF (25 mL). Chloroform (1.5 mL) and platinum oxide (70 mg) are added and the mixture subjected to hydrogenation at 5 atmospheres in a Parr hydrogenation apparatus. After 4 hours the mixture is filtered through celite and the celite bed washed with absolute ethanol (2×20 mL). The filtrate and washings are evaporated in vacuo to give a product which is purified by column chromatography to provide the title compound 30.

Workup

  1. filtrationAfter 4 hours the mixture is filtered through celite
  2. washthe celite bed washed with absolute ethanol (2×20 mL)
  3. customThe filtrate and washings are evaporated in vacuo
  4. customto give a product which
  5. customis purified by column chromatography

Sources & evidence

ORD record
ord-dc6622030a3c4418b2bb510f7562c1b1
Source dataset
uspto-grants-2003_08
Patent number
US06610663B2

Reaction notes

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