1-Chloro-2,4-Dinitrobenzene → HCID 58653700, compound

HRID 1676076Notes

Reaction equation

HRID 1676076 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1Cl)([O-:3])=[O:2].[NH2:14][C@@H:15]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:16][C:17]([O:19][CH3:20])=[O:18].C(N(CC)CC)C>CO>[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[NH:14][C@@H:15]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:16][C:17]([O:19][CH3:20])=[O:18])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 61-Chloro-2,4-DinitrobenzeneHCID 8471TriethylamineHCID 788100methyl (3R)-3-amino-3-phenylpropanoate

Product 1

HCID 58653700HCID 58653700, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2,4-dinitrochlorobenzene (5.1 g, 25 mmol) in methanol (60 mL) was added methyl (3R)-3-amino-3-phenylpropanoate (3.75 g, 21 mmol, prepared according to Davies et. al., Tetrahedron Asymm., 1991, 183) and triethylamine (2.9 mL, 21 mmol). The mixture was brought to reflux, heating in total for 5 hours, and was then cooled and evaporated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (95:5), to afford the title compound, [LCMS (Method C, Mobile Phase I) RT=3.22 mins, MH+ 346].

Workup

  1. temperatureto reflux
  2. temperatureheating in total for 5 hours
  3. temperaturewas then cooled
  4. customevaporated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel
  6. washeluting with a mixture of dichloromethane and methanol (95:5)

Sources & evidence

ORD record
ord-5656dd9930ad4879960bc9e7bf981ee8
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

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