HCID 67454416, compound → HCID 67456175, compound

HRID 1713265Notes

Reaction equation

HRID 1713265 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>C(O)C.O1CCCC1.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[CH:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 67454416HCID 67454416, compound

Product 1

HCID 67456175HCID 67456175, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of tert-butyl N-(3′-bezyloxy-biphenyl-4-ylmethyl)carbamate (1.16 g) in ethanol/tetrahydrofuran (4/1, 30 mL) was added 10% palladium-on carbon (55.4 wt % H2O, 0.520 g), and the resulting mixture was stirred at 30° C. for 5 hours under a hydrogen atmosphere. The insoluble material was filtered out and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=5/2) to give the title compound (0.731 g).

Workup

  1. filtrationThe insoluble material was filtered out
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=5/2)

Sources & evidence

ORD record
ord-55b5c87d9b5e4a63b67cc51314548f97
Source dataset
uspto-grants-2010_09
Patent number
US07795236B2

Reaction notes

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