Potassium Carbonate → 5-[2-(Tert-butoxycarbonyl-methyl-amino)-propyl]-benzo[1,3]dioxole-2-carboxylic acid ethyl ester

HRID 1828961Notes

Reaction equation

[C:1]([O:5][C:6](=[O:20])[N:7]([CH:9]([CH3:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([OH:18])[CH:12]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH:28](Br)[C:29]([O:31][CH2:32][CH3:33])=[O:30]>CN(C)C=O>[CH2:32]([O:31][C:29]([CH:28]1[O:17][C:14]2[CH:15]=[CH:16][C:11]([CH2:10][CH:9]([N:7]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:20])[CH3:8])[CH3:19])=[CH:12][C:13]=2[O:18]1)=[O:30])[CH3:33]

Participants

Conditions

Temperature: 100 °C

Procedure

To 2.5 g (8.8 mmol) of 1C was added 20 mL of anhydrous N,N-dimethylformamide (DMF) followed by 3.68 g (26 mmol) of anhydrous K2CO3 and 3 mL (23 mmol) of ethyl dibromoacetate. The reaction mixture was heated to 100° C. for 4.5 hours and then allowed to cool to room temperature. This was concentrated to dryness under reduced pressure, and 50 mL of water was added to the residue. The mixture was adjusted to pH 3 using 1N HCl and extracted with 4×50 mL of dichloromethane. Organic layers were combined, dried (anhydrous Na2SO4), and concentrated to dryness. The residue was purified by flash column silica gel chromatography using 15% ethyl acetate in hexane to give 1.1 g (3.01 mmol, 34%) of 1D as a colorless oil (M+Na, 388).

Workup

temperatureto cool to room temperature
concentrationThis was concentrated to dryness under reduced pressure, and 50 mL of water
additionwas added to the residue
extractionextracted with 4×50 mL of dichloromethane
dry with materialdried (anhydrous Na2SO4)
concentrationconcentrated to dryness
customThe residue was purified by flash column silica gel chromatography

Sources & evidence

ORD record: ord-9af2de2fdd83484d93496d9459e74eed
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07060847B2

Reaction notes

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