HCID 44599421, compound → HCID 67080370, compound

HRID 1021394Notes

Reaction equation

HRID 1021394 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:32])[NH:20][CH2:21][CH2:22]/[CH:23]=[CH:24]\[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[Cl:31])=[CH:15][CH:14]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:33]([O-:35])=[O:34].[Na+:36].[H][H]>CO.[Pt](=O)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:14]=[CH:15][C:16]([C:19](=[O:32])[NH:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[Cl:31])=[CH:17][CH:18]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:33]([O-:35])=[O:34].[Na+:36]

Participants

5

Reactant 2

HCID 44599421HCID 44599421, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67080370HCID 67080370, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

To a solution of sodium (Z)-6-chloro-7-(4-(4-(2-chlorophenyl)but-3-enylcarbamoyl)phenoxy)chroman-4-carboxylate (0.16 g, 0.31 mmol) in methanol (2 mL) was added platinum(IV) oxide (0.018 g, 0.079 mmol), and to the resulting stirred mixture at ambient temperature was fitted a balloon of hydrogen. The flask was purged and refilled five times with hydrogen, and the resulting mixture was stirred at ambient temperature under a balloon of hydrogen for 30 minutes, by which time the catalyst had clumped up. The methanol supernatant was decanted away from the catalyst with a pipet and concentrated, and the residue concentrated from diethyl ether to afford sodium 6-chloro-7-(4-(4-(2-chlorophenyl)butylcarbamoyl)phenoxy)chroman-4-carboxylate as a white glass (142 mg, 87% yield). MS (apci) m/z=514.1 (M+2H-Na).

Workup

  1. customThe flask was purged
  2. additionrefilled five times with hydrogen
  3. stirringthe resulting mixture was stirred at ambient temperature under a balloon of hydrogen for 30 minutes, by which time the catalyst
  4. customThe methanol supernatant was decanted away from the catalyst with a pipet
  5. concentrationconcentrated
  6. concentrationthe residue concentrated from diethyl ether

Sources & evidence

ORD record
ord-c9b6e004763e40abb861287797f45819
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

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