HCID 53813835, compound → HCID 56979796, compound

HRID 899766Notes

Reaction equation

HRID 899766 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:10]=[CH:11][C:12]([O:14][CH3:15])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6]([NH:8][CH:9]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 53813835HCID 53813835, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 56979796HCID 56979796, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 4-[(t-butoxycarbonyl)-amino]-4-phenylbut-2-enoate (3.17 g) in methanol (100 mL) was added palladium on carbon (250 mg (10% by wt. Pd)). The mixture was then placed under 50 psig hydrogen gas, and was shaken on a Parr hydrogenator for 2 hours. The mixture was then filtered through celite, concentrated in vacuo and purified by silica gel flash chromatography (3:1 hexanes:ethyl acetate) to afford methyl 4-[(t-butoxycarbonyl)-amino]-4-phenylbutanoate as a pale yellow oil in a yield of 2.61 g (82%). 1H NMR (CDCl3) δ 1.45 (s, 9H), 2.07 (m, 2H), 2.36 (m, 2H), 3.69 (s, 3H), 4.59 (m, 1H), 5.15 (br s, 1H (NH)), 7.21-7.34 (m, 5H).

Workup

  1. filtrationThe mixture was then filtered through celite
  2. concentrationconcentrated in vacuo
  3. custompurified by silica gel flash chromatography (3:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-36ca4b85ca494d6abbe4e7d92dde79e7
Source dataset
uspto-grants-2008_04
Patent number
US07354934B2

Reaction notes

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