HCID 67363471, compound → HCID 67364561, compound

HRID 1516181Notes

Reaction equation

HRID 1516181 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][N:6]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[N+:15]([O-])=O)[CH3:2].[H][H]>C(OCC)(=O)C.[Pd].[Br-].[Zn+2].[Br-]>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][N:6]([CH2:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[NH2:15])[C:18]([O:20][C:21]([CH3:24])([CH3:22])[CH3:23])=[O:19])[CH3:2]

Participants

6

Reactant 2

HCID 67363471HCID 67363471, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67364561HCID 67364561, compoundYield 95.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 10421208Zinc bromideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of [tert-butoxycarbonyl-(5-chloro-2-nitro-benzyl)-amino]-acetic acid ethyl ester (69.0 g, 0.186 mol) in ethyl acetate (1200 ml) was added zinc bromide (8.5 g, 0.037 mol). The reaction mixture was purged with argon after 15 min. After addition of the palladium catalyst (10% on activated charcoal, 7.9 g, 0.0074 mol) the mixture was hydrogenated at ambient pressure during a period of ca. 48 h until ca. 13 l of hydrogen gas had been consumed. The catalyst was removed by filtration and the filtrate was washed with two portions of saturated aqueous sodium bicarbonate solution and brine, each. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound (60.6 g, 95.5%) as yellow waxy solid. MS m/e: 343 (M+H+).

Workup

  1. customThe reaction mixture was purged with argon after 15 min
  2. customhad been consumed
  3. customThe catalyst was removed by filtration
  4. washthe filtrate was washed with two portions of saturated aqueous sodium bicarbonate solution and brine
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ec5ea9947a5d4f90aa5ab7974097e9be
Source dataset
uspto-grants-2012_07
Patent number
US08227458B2

Reaction notes

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