Methyl 2-[(2,6-dichlorobenzyl)amino]-3-(4-nitrophenyl)propanoate → HCID 11302630, compound

HRID 1869787

Reaction equation

HRID 1869787 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:3]=1[CH2:4][NH:5][CH:6]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8]>CC(O)=O>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][CH:6]([NH:5][CH2:4][C:3]2[C:21]([Cl:25])=[CH:22][CH:23]=[CH:24][C:2]=2[Cl:1])[C:7]([O:9][CH3:10])=[O:8])=[CH:13][CH:14]=1

Participants

3

Reactant 1

HCID 11269078Methyl 2-[(2,6-dichlorobenzyl)amino]-3-(4-nitrophenyl)propanoate

Product 1

HCID 11302630HCID 11302630, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To methyl 2-[(2,6-dichlorobenzyl)amino]-3-(4-nitrophenyl)propanoate 7a (8.2 g) solubilized in CH3COOH in an ultrasonic bath is added PtO2 hydrate (typical Pt content 79-84%) (0.02 g). A H2 pressure of 15 psi is then applied at RT and consumed after 5 min. An other H2 pressure of 10 psis is then applied at RT and consumed after 5-10 min. A H2 pressure of 10 psis is again applied at RT and a stabilization is observed after 5 min. The catalyst is filtered over celite under nitrogen and washed with CH3COOH. The solvent is evaporated. AcOEt (200 ml) is added to the residue and this organic phase is washed three times with saturated NaHCO3 (200 ml), dried over MgSO4 and evaporated. The residue is purified by silica gel chromatography using CH2Cl2/CH3OH/NH4OH cc (99.75/0.25/0.025) as eluent.

Workup

  1. customis then applied at RT
  2. customconsumed after 5 min
  3. customis then applied at RT
  4. customconsumed after 5-10 min
  5. customis again applied at RT
  6. filtrationThe catalyst is filtered over celite under nitrogen
  7. washwashed with CH3COOH
  8. customThe solvent is evaporated
  9. additionAcOEt (200 ml) is added to the residue
  10. washthis organic phase is washed three times with saturated NaHCO3 (200 ml)
  11. dry with materialdried over MgSO4
  12. customevaporated
  13. customThe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-66d3d69161b541ca8addcd5fcf33d69f
Source dataset
uspto-grants-2009_12
Patent number
US07638630B2

Linked notes

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