Tin atom → 1,1-Dimethyl-ethyl-(6-amino-2,3-dichlorobenzyl)glycine

HRID 41352Notes

Reaction equation

HRID 41352 reaction equation
[Sn].[CH3:2][C:3]([N:6]([CH2:11][C:12]1[C:17]([N+:18]([O-])=O)=[CH:16][CH:15]=[C:14]([Cl:21])[C:13]=1[Cl:22])[CH2:7][C:8]([OH:10])=[O:9])([CH3:5])[CH3:4]>[Pd].[Pt].[Pt]=O.[Rh]>[CH3:5][C:3]([N:6]([CH2:11][C:12]1[C:17]([NH2:18])=[CH:16][CH:15]=[C:14]([Cl:21])[C:13]=1[Cl:22])[CH2:7][C:8]([OH:10])=[O:9])([CH3:2])[CH3:4]

Participants

7

Reactant 2

HCID 5352426Tin atomHCID 67446873HCID 67446873, compound2×

Product 1

HCID 674478021,1-Dimethyl-ethyl-(6-amino-2,3-dichlorobenzyl)glycine

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 23939PlatinumCatalystHCID 23948RhodiumCatalystHCID 82844Platinum oxide (PtO)Catalyst

Procedure

Where possible, the invention seeks to avoid the use of a tin-reagent to effect the reduction. Thus in another procedure according to the invention, 1,1-dimethyl-ethyl N-(2,3-dichloro-6-nitrobenzyl)glycine (compound XXII) may also be catalytically hydrogenated using a metal or metal-based catalyst such as platinum, platinum oxide, rhodium, and palladium on carbon under hydrogen pressure. The catalyst is then removed by filtration and the filtrate concentrated, diluted with water and an organic solvent and basified using an alkali to a pH of about 9-10. The organic phase is separated and concentrated and the crude material purified by low temperature recrystallization to give 1,1-dimethyl-ethyl-(6-amino-2,3-dichlorobenzyl)glycine.

Workup

  1. customThe catalyst is then removed by filtration
  2. concentrationthe filtrate concentrated
  3. additiondiluted with water
  4. customThe organic phase is separated
  5. concentrationconcentrated
  6. customthe crude material purified by low temperature recrystallization

Sources & evidence

ORD record
ord-d7108790b9864192afef2d127831073c
Source dataset
uspto-grants-2013_09
Patent number
US08530651B2

Reaction notes

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