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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1664285Generated: October 31, 2026

1,2-Dichloroethane → (Z)-N-((2R,4R,6R)-2-Methoxy-2-((R)-3-(4-methoxybenzyl)-2-oxothiazolidin-4-yl)-6-(pent-4-enyl)-tetrahydro-2H-pyran-4-yl)-3-methylhepta-2,6-dienamide

https://huagongshe.com/reaction/1664285

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,2-DichloroethaneHCID 11—
Reactant1-HydroxybenzotriazoleHCID 75771—
Reactant(2Z)-3-Methylhepta-2,6-dienoic acidHCID 13947388—
Reactant(R)-4-((2R,4R,6R)-4-Amino-2-methoxy-6-(pent-4-enyl)-tetrahydro-2H-pyran-2-yl)-3-(4-methoxybenzyl)thiazolidin-2-oneHCID 59644046—
SolventDichloromethaneHCID 6344—
Product(Z)-N-((2R,4R,6R)-2-Methoxy-2-((R)-3-(4-methoxybenzyl)-2-oxothiazolidin-4-yl)-6-(pent-4-enyl)-tetrahydro-2H-pyran-4-yl)-3-methylhepta-2,6-dienamideHCID 5964404767%

Reaction Steps

A solution of the title compound from Example 67 (155 mg, 0.368 mmol) in dichloromethane (5 mL) was treated with the title compound from Example 21 (58 mg, 0.42 mmol), HOBT (65 mg, 0.42 mmol), and EDC (78 mg, 0.41 mmol), and the mixture was stirred at room temperature for 4 days. The mixture was then concentrated and the residue was chromatographed on silica, eluting with ethyl acetate/hexanes, which afforded the title compound (133 mg, 67%) as a crystalline solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08039465B2
Source datasetuspto-grants-2011_10
ORD IDord-544424ae8c7f4c5c936bd90ab5dfbc99
Source noteuspto-grants-2011_10