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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 900626Generated: October 31, 2026

4-Acetamido-3-chlorobenzoic acid → 1-[2-(4-Acetylamino-3-chloro-benzoylamino)-propionyl]-piperidine-2-carboxylic acid (2-benzyloxy-5-oxo-tetrahydro-furan-3-yl)amide

https://huagongshe.com/reaction/900626

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-Acetamido-3-chlorobenzoic acidHCID 680951—
Reactant1-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (5-oxo-2-phenethyloxy-tetrahydro-furan-3-yl)-amideHCID 22977512—
Reactant{2-[2-(2-Benzyloxy-5-oxo-tetrahydro-furan-3-ylcarbamoyl)-piperidin-1-yl]-1-methyl-2-oxo-ethyl}-carbamic acid tert-butyl esterHCID 22977789—
Product1-[2-(4-Acetylamino-3-chloro-benzoylamino)-propionyl]-piperidine-2-carboxylic acid (2-benzyloxy-5-oxo-tetrahydro-furan-3-yl)amideHCID 8659056047%

Reaction Steps

Prepared from {2-[2-(2-benzyloxy-5-oxo-tetrahydro-furan-3-ylcarbamoyl)-piperidin-1-yl]-1-methyl-2-oxo-ethyl}-carbamic acid tert butyl ester and 4-acetylamino-3-chlorobenzoic acid by the procedure used in the preparation of 98a to give the title compound (71 mg, 47% yield). 1H-NMR (500 MHz, CDCl3) δ 1.10-1.97 (m, 10H), 2.10-2.68 (m, 5H), 2.73-3.24 (m, 2H), 3.62-3.92 (m, 1H), 4.24-5.27 (m, 5H), 5.48-5.59 (m, 0.5H), 5.75-5.85 (m, 0.5H), 6.51-6.61 (d, 1H), 7.05-7.45 (m, 4H), 7.52-8.12 (m, 4H). Analytical HPLC 8.30 min. LC-MS (ES+) m/e=585.3 (MH+).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07358273B2
Source datasetuspto-grants-2008_04
ORD IDord-1e611adb977c4089b4a383cb1467d368
Source noteuspto-grants-2008_04