1,2-Dichloroethane → HCID 86628750, compound

HRID 1360100Notes

Reaction equation

HRID 1360100 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:11])[C@H:5]([CH2:7][CH2:8][CH2:9][CH3:10])[NH2:6].[C:12](O)(=[O:17])[CH2:13][CH2:14][CH:15]=[CH2:16].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O.C(OCC)C>[CH3:2][O:3][C:4](=[O:11])[C@H:5]([CH2:7][CH2:8][CH2:9][CH3:10])[NH:6][C:12](=[O:17])[CH2:13][CH2:14][CH:15]=[CH2:16]

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 611384-Pentenoic acidHCID 757711-HydroxybenzotriazoleHCID 14039065methyl (2S)-2-aminohexanoate hydrochloride

Product 1

HCID 86628750HCID 86628750, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of L-norleucine methyl ester hydrochloride (0.50 g, 2.75 mmol) and 4-pentenoic acid (0.33 g, 3.30 mmol) in DMF (5 mL) was added EDC (0.79 g, 4.13 mmol) and HOBt (0.56 g, 4.13 mmol). The reaction mixture was stirred at 50° C. for 15 h, cooled and poured onto a mixture of ethyl ether and water. The organic layer was washed with water, dried over NaSO4, filtered and concentrated. The crude product was purified by silica gel chromatography (gradient elution 10% to 90% ethyl acetate in hexanes) to give N-pent-4-enoyl-L-norleucine methyl ester.

Workup

  1. temperaturecooled
  2. washThe organic layer was washed with water
  3. dry with materialdried over NaSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel chromatography (gradient elution 10% to 90% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-47ec5c429ddd454886585d282a0aa059
Source dataset
uspto-grants-2011_02
Patent number
US07879797B2

Reaction notes

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