Ethyl Acrylate → HCID 59038199, compound

HRID 1058227Notes

Reaction equation

HRID 1058227 reaction equation
[OH:1][C@@:2]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([CH3:24])[C:3]([N:5]1[CH2:23][CH2:22][CH2:21][C@H:6]1[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[CH2:18][CH2:19][NH2:20])=[O:8])=[O:4].[C:31]([O:35][CH2:36][CH3:37])(=[O:34])[CH:32]=[CH2:33]>CCO>[OH:1][C@@:2]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)([CH3:24])[C:3]([N:5]1[CH2:23][CH2:22][CH2:21][C@H:6]1[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[CH2:18][CH2:19][NH:20][CH2:33][CH2:32][C:31]([O:35][CH2:36][CH3:37])=[O:34])=[O:8])=[O:4]

Participants

4

Reactant 2

HCID 8821Ethyl AcrylateHCID 59038228HCID 59038228, compound

Product 1

HCID 59038199HCID 59038199, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 1-((2R)-2-hydroxy-2-phenylpropanoyl)-N-(2-(2-aminoethyl)-5-chlorobenzyl)-L-prolinamide (90 mg, 0.21 mmol) in EtOH (2 mL) was added ethyl acrylate (25 microliters, 0.22 mmol). The mixture was stirred at ambient temperature for 48 h. The solvent was removed under reduced pressure and the residue was purified by flash silica gel column chromatography using a gradient elution of 5% to 7.5% MeOH in CH2Cl2. The product-containing fractions were combined to give the title compound as an amorphous solid upon removal of the solvents in vacuo (TLC Rf=0.4 (95:5 CH2Cl2:MeOH); HPLC RT=2.95 min, method A; LC-MS m/z=530).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by flash silica gel column chromatography
  3. washa gradient elution of 5% to 7.5% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-046ca5df93254398a1c33f0e5f5127ed
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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