Diisopropylethylamine → HCID 58497456, compound

HRID 2175171Notes

Reaction equation

HRID 2175171 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6](Cl)[CH:5]=[C:4]([CH3:12])[N:3]=1.Cl.[CH2:14]([O:16][C:17](=[O:27])[CH2:18][C@@H:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:15].CCN(C(C)C)C(C)C>CC(N(C)C)=O.C(OCC)(=O)C>[CH2:14]([O:16][C:17](=[O:27])[CH2:18][C@@H:19]([NH:26][C:6]1[CH:5]=[C:4]([CH3:12])[N:3]=[C:2]([Cl:1])[C:7]=1[N+:8]([O-:10])=[O:9])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH3:15]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2734508ethyl (3R)-3-amino-3-phenylpropanoate hydrochlorideHCID 27848192,4-Dichloro-6-methyl-3-nitropyridine

Product 1

HCID 58497456HCID 58497456, compoundYield 51.3%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 2,4-dichloro-6-methyl-3-nitropyridine (900 mg, 4.35 mmol) in DMA (8 mL) were added (R)-3-amino-3-phenylpropionic acid ethyl ester HCl (799 mg, 3.48 mmol) and DIPEA (1.6 mL, 8.70 mmol). The reaction mixture was stirred at room temperature for 12 hours. The reaction was then diluted with ethyl acetate and washed with water twice. The organic phase was dried over Na2SO4 and concentrated to give yellow oil. The resulting oily residue was purified by silica gel preparative TLC using 99:1 CH2Cl2:MeOH as an eluent to afford 650 mg (51%) of the title compound as a light orange oil. LCMS, M++1, m/z: 364.15.

Workup

  1. washwashed with water twice
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated
  4. customto give yellow oil
  5. customThe resulting oily residue was purified by silica gel preparative TLC

Sources & evidence

ORD record
ord-9a91c91768f347868d3ed6c22ae77413
Source dataset
uspto-grants-2015_06
Patent number
US09062056B2

Reaction notes

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