HCID 66865525, compound → HCID 66864547, compound

HRID 1628176Notes

Reaction equation

HRID 1628176 reaction equation
C([O:8][C:9](=[O:27])[C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])([CH3:19])[CH3:18])=[CH:12][CH:11]=1)C1C=CC=CC=1>CCOC(C)=O.[Pd]>[C:23]([O:22][C:20]([C:17]([CH3:19])([O:16][C:13]1[CH:12]=[CH:11][C:10]([C:9]([OH:27])=[O:8])=[CH:15][CH:14]=1)[CH3:18])=[O:21])([CH3:24])([CH3:25])[CH3:26]

Participants

4

Reactant 1

HCID 66865525HCID 66865525, compound

Product 1

HCID 66864547HCID 66864547, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-(1-tert-Butoxycarbonyl-1-methyl-ethoxy)-benzoic acid benzyl ester (2.75 g, 7.42 mmol) was dissolved in EtOAc and Pd/C (10% Pd, ca. 100 mg) was added. The reaction vessel was evacuated and connected to a hydrogen line. After 3 h stirring at r.t. under H2 atmosphere the catalyst was filtered off and the filtrate was evaporated. The crude product was used in the next step without further purification (2.0 g, 96.1%). 1H NMR (500 MHz, CDCl3): δ 7.99 (d, 2H), 6.84 (d, 2H), 1.62 (s, 6H), 1.41 (s, 9H).

Workup

  1. customThe reaction vessel was evacuated
  2. filtrationwas filtered off
  3. customthe filtrate was evaporated
  4. customThe crude product was used in the next step without further purification (2.0 g, 96.1%)

Sources & evidence

ORD record
ord-970adacea1474be98c8dc3940fccd56d
Source dataset
uspto-grants-2014_07
Patent number
US08785681B2

Reaction notes

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