Diisopropylethylamine → HCID 46179257, compound

HRID 1624176Notes

Reaction equation

HRID 1624176 reaction equation
[CH3:1][O:2][C:3](/[CH:5]=[CH:6]/[C:7]([O:9][CH2:10][C:11]([OH:13])=O)=[O:8])=[O:4].Cl.CN(C)CCCN=C=NCC.Cl.[CH2:27]([O:29][CH2:30][CH2:31][NH:32][CH2:33][CH2:34][O:35][CH2:36][CH3:37])[CH3:28].C(N(C(C)C)CC)(C)C>ClCCl>[C:7]([O:9][CH2:10][C:11](=[O:13])[N:32]([CH2:33][CH2:34][O:35][CH2:36][CH3:37])[CH2:31][CH2:30][O:29][CH2:27][CH3:28])(=[O:8])/[CH:6]=[CH:5]/[C:3]([O:2][CH3:1])=[O:4]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86639352HCID 86639352, compoundHCID 86639353HCID 86639353, compound

Product 1

HCID 46179257HCID 46179257, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following general procedure B2, 2-[(2E)-3-(methoxycarbonyl)prop-2-enoyloxy]acetic acid (23) (0.80 g, 6.14 mmol) was activated with N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDAC) (1.40 g, 7.37 mmol) in 20 mL of dichloromethane (DCM) at ca. 0° C. bis(2-Ethoxyethyl)amine hydrochloride (1.18 g, 7.37 mmol) (1.18 g, 7.37 mmol) and diisopropylethylamine (DIEA) (1.34 mL, 0.99 g, 7.67 mmol) were added to the activated carboxylic acid. After work-up and isolation, and purification by silica gel flash column chromatography (Biotage) using ethyl acetate (EtOAc) and hexanes (1:1) afforded 0.30 g (15% yield) of the title compound (27) as a white solid. 1H NMR (CDCl3, 400 MHz): δ 6.97 (d, J=15.6 Hz, 1H), 6.94 (d, J=1.6 Hz, 1H), 5.01 (s, 2H), 3.80 (s, 3H), 3.56-3.43 (m, 12H), 1.19 (q, J=7.6 Hz, 6H). MS (ESI): m/z 332.20 (M+H)+.

Workup

  1. customAfter work-up and isolation, and purification by silica gel flash column chromatography (Biotage)

Sources & evidence

ORD record
ord-57cba52b456a4c858e00c9456d5d9d41
Source dataset
uspto-grants-2014_07
Patent number
US08778991B2

Reaction notes

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