1,2-Dichloroethane → HCID 54397258, compound

HRID 1953595Notes

Reaction equation

HRID 1953595 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C@H:11]([C:16]([OH:18])=[O:17])[CH2:12][CH2:13][S:14][CH3:15])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:19](O)[CH:20]([CH3:22])[CH3:21].C(Cl)CCl>O1CCOCC1.CN(C1C=CN=CC=1)C>[CH2:19]([O:17][C:16](=[O:18])[C@H:11]([CH2:12][CH2:13][S:14][CH3:15])[NH:10][C:8](=[O:9])[CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH:20]([CH3:22])[CH3:21]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 6560IsobutanolHCID 13521048HCID 13521048, compound

Product 1

HCID 54397258HCID 54397258, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
23 °C

Procedure

N-phenylacetyl-L-methionine (0.1285 g, 0.447 mmol) was dissolved in 3.0 mL dioxane and iso-butyl alcohol (0.2 mL) and treated with EDC (0.094 g, 0.492 mmol), and catalytic DMAP (0.015 g). After stirring for 17 hours at 23° C., the mixture was evaporated at reduced pressure to an oil, the residue was diluted in EtOAc and washed with 0.1 N HCl and saturated sodium bicarbonate. Chromatography on silica gel using 98:2 CHCl3 /MeOH as eluant provided the pure product.

Workup

  1. customthe mixture was evaporated at reduced pressure to an oil
  2. additionthe residue was diluted in EtOAc
  3. washwashed with 0.1 N HCl and saturated sodium bicarbonate
  4. customChromatography on silica gel using 98:2 CHCl3 /MeOH as eluant provided the pure product

Sources & evidence

ORD record
ord-08bb4bd8522c44c3aa72832dc09ea390
Source dataset
uspto-grants-2000_09
Patent number
US06117901

Reaction notes

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