1,2-Dichloroethane → HCID 86760514, compound

HRID 1295483Notes

Reaction equation

HRID 1295483 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C@H:11]([O:17][CH2:18][CH3:19])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=1.[C:20](O)(=[O:27])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C(Cl)CCl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:18]([O:17][C@@H:11]([CH2:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][NH:1][C:20](=[O:27])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:5][CH:6]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH3:19]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 8094Heptanoic AcidHCID 86760512HCID 86760512, compound

Product 1

HCID 86760514HCID 86760514, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Ethyl (2S)-3-[4-(2-aminoethyl)phenyl]-2-ethoxypropanoate (320 mg 1.206 mmol) and heptanoic acid (157 mg, 1.206 mmol) were mixed in DCM (10 ml). EDC (243 mg, 1.266 mmol) was added and then DMAP (147 mg, 1.206 mmol) was added. The mixture was stirred at room temperature overnight. It was then washed with 1% hydrochloric acid, water, 1% sodium hydrogencarbonate aqueous solution, water and brine and dried with magnesium sulfate. The solvent was evaporated in vacuum. Chromatography of the residue on a column (ISOLUTE, SI, 2 g/6 ml) using DCM, MeOH/DCM (0.5:99.5) and then MeOH/DCM (1:99) as eluant gave 166 mg desired product, yield 37%.

Workup

  1. washIt was then washed with 1% hydrochloric acid, water, 1% sodium hydrogencarbonate aqueous solution, water and brine
  2. dry with materialdried with magnesium sulfate
  3. customThe solvent was evaporated in vacuum

Sources & evidence

ORD record
ord-9272f9927ba3429fb42e0598be5dddd8
Source dataset
uspto-grants-2007_07
Patent number
US07241923B2

Reaction notes

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