HCID 66865525, compound → HCID 66864547, compound

HRID 709491Notes

Reaction equation

HRID 709491 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-0182d6db8b1a4d688e0957f0eae5af9e
Source dataset
uspto-grants-2015_11
Patent number
US09181181B2

Reaction notes

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