Ethylacetate methanol → HCID 22285666, compound

HRID 1062465Notes

Reaction equation

HRID 1062465 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([Cl:27])[C:15]=1[O:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([CH:24]([CH3:26])[CH3:25])[CH:18]=1)[CH:5]=[C:6]1[S:10][C:9](=[O:11])[NH:8][C:7]1=[O:12].[C:28](OCC)(=O)C.CO>[Pd]>[Cl:27][C:14]1[CH:13]=[C:4]([CH:3]=[C:2]([Cl:1])[C:15]=1[O:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:28])=[C:19]([CH:24]([CH3:25])[CH3:26])[CH:18]=1)[CH2:5][CH:6]1[S:10][C:9](=[O:11])[NH:8][C:7]1=[O:12]

Participants

4

Reactant 2

HCID 21584119Ethylacetate methanolHCID 86584086HCID 86584086, compound

Product 1

HCID 22285666HCID 22285666, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of the title compound from Step D (31 mg, 0.072 mmol) was dissolved in ethyl acetate/methanol (1 ml/1 ml) and placed in a hydrogenation bottle with 10% palladium on carbon (90 mg). The mixture was placed on Parr shaker for two hours under 50 p.s.i. of hydrogen, then filtered through diatomaceous earth, and the filter cake was washed with ethyl acetate/methanol. The combined filtrate was concentrated to give the title compound (26 mg) as a clear, viscous oil that was used in the next step without purification. MS (APCI−) Calc: 439.0, Found: 438.1 (M−1).

Workup

  1. filtrationof hydrogen, then filtered through diatomaceous earth
  2. washthe filter cake was washed with ethyl acetate/methanol
  3. concentrationThe combined filtrate was concentrated

Sources & evidence

ORD record
ord-6267144ae3734e74bd19c88f719fd2bd
Source dataset
uspto-grants-2005_11
Patent number
US06960604B2

Reaction notes

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