Diethyl acetylenedicarboxylate → HCID 178472244, compound

HRID 1664199Notes

Reaction equation

[Cl:1][CH2:2][CH2:3][O:4][CH2:5][C:6]1([C:12](=[NH:15])[NH:13][OH:14])[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1.[C:16]([C:23]([O:25][CH2:26][CH3:27])=[O:24])#[C:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>>[Cl:1][CH2:2][CH2:3][O:4][CH2:5][C:6]1([C:12](=[NH:15])[NH:13][O:14][C:16](=[CH:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:7][CH2:8][O:9][CH2:10][CH2:11]1

Participants

Reactant 2

HCID 69803Diethyl acetylenedicarboxylate

HCID 178513392HCID 178513392, compound

Product 1

HCID 178472244HCID 178472244, compoundYield 84%

Procedure

Reaction of 4-((2-chloroethoxy)methyl)-N-hydroxytetrahydro-2H-pyran-4-carboximidamide (10.50 g, 44.36 mmol) with diethyl acetylenedicarboxylate gave 15.25 g (84% yield) of title material as light yellow oil after chromatography. 1HNMR 400 MHz (CDCl3) δ (ppm): (mixture of E/Z isomers ratio˜3:2) 1.25-1.4 (6H, quartet of triplets), 1.6 (2H, m), 2.05 (2H, m), 3.52 (1H, s), 3.54 (1H, s), 3.65-3.85 (8H, m), 4.16-4.23 (2H, m), 4.28-4.41 (2H, m), 5.33 (1H, broad s), 5.59 (1H, broad s), 5.64 (1H, s), 5.78 (1H, s). MS (ESI+) m/e 407 [M+H+].

Sources & evidence

ORD record: ord-2a5774bca4984c679cb2cdd866387ca6
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039458B2

Reaction notes

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