Ethanol → HCID 69055975, compound

HRID 1785391Notes

Reaction equation

HRID 1785391 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[C:14]([CH2:16][C:17]#[N:18])[CH:13]=[CH:12][N:11]3[C:19]=2[C:20]2[CH:25]=[CH:24][N:23]=[C:22]([S:26]([CH3:29])(=[O:28])=[O:27])[N:21]=2)=[CH:4][CH:3]=1.C(O)C.[H][H]>O=[Pt]=O.C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[C:14]([CH2:16][CH2:17][NH2:18])[CH:13]=[CH:12][N:11]3[C:19]=2[C:20]2[CH:25]=[CH:24][N:23]=[C:22]([S:26]([CH3:29])(=[O:28])=[O:27])[N:21]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 69060209HCID 69060209, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 69055975HCID 69055975, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalyst2×HCID 6212ChloroformSolvent

Procedure

A 300 mL pressure bottle containing nitrile 22 (980 mg, 2.41 mmol) was charged with ethanol (18 mL), chloroform (2 mL), and then PtO2 (200 mg, 0.881 mmol). The pressure bottle was then sealed, then charged with 50 psi hydrogen, and the reaction mixture was allowed to stir at room temperature for 12 hours, after which additional PtO2 (500 mg, 1.14 mmol) was added, and an the pressure bottle was charged with an additional 50 psi hydrogen then sealed, and the reaction mixture was stirred at room temperature for 3 hours. At this point, TLC analysis showed the reaction to be complete. The reaction mixture was then filtered through successive 0.45 □m Gelman nylon acrodiscs. The filtrate was then concentrated under reduced pressure and carried onto the next step without further purification. Crude yield of 23: 1.20 g (121%). MS (ESI+) 412.2.

Workup

  1. customThe pressure bottle was then sealed
  2. customthen sealed
  3. stirringthe reaction mixture was stirred at room temperature for 3 hours
  4. customthe reaction
  5. filtrationThe reaction mixture was then filtered through successive 0.45 □m Gelman nylon acrodiscs
  6. concentrationThe filtrate was then concentrated under reduced pressure
  7. customcarried onto the next step without further purification

Sources & evidence

ORD record
ord-2045dab18e114bea8b0f18ec60021110
Source dataset
uspto-grants-2009_03
Patent number
US07504501B2

Reaction notes

Loading…