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

HRID 900626Notes

Reaction equation

HRID 900626 reaction equation
C(O[C:6](=[O:35])[NH:7][CH:8]([CH3:34])[C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[C:17](=[O:33])[NH:18][CH:19]1[CH2:23][C:22](=[O:24])[O:21][CH:20]1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:10])(C)(C)C.[C:36]([NH:39][C:40]1[CH:48]=[CH:47][C:43](C(O)=O)=[CH:42][C:41]=1[Cl:49])(=[O:38])[CH3:37].O=C1OC(OCCC2C=CC=CC=2)C(NC(C2CCCN2C(=O)C(NC(=O)C2C=CC(N)=C(Cl)C=2)C)=O)C1>>[CH2:26]([O:25][CH:20]1[CH:19]([NH:18][C:17]([CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][N:11]2[C:9](=[O:10])[CH:8]([NH:7][C:6](=[O:35])[C:43]2[CH:47]=[CH:48][C:40]([NH:39][C:36](=[O:38])[CH3:37])=[C:41]([Cl:49])[CH:42]=2)[CH3:34])=[O:33])[CH2:23][C:22](=[O:24])[O:21]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 3

HCID 6809514-Acetamido-3-chlorobenzoic acidHCID 229775121-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (5-oxo-2-phenethyloxy-tetrahydro-furan-3-yl)-amideHCID 22977789{2-[2-(2-Benzyloxy-5-oxo-tetrahydro-furan-3-ylcarbamoyl)-piperidin-1-yl]-1-methyl-2-oxo-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 865905601-[2-(4-Acetylamino-3-chloro-benzoylamino)-propionyl]-piperidine-2-carboxylic acid (2-benzyloxy-5-oxo-tetrahydro-furan-3-yl)amideYield 47%

Procedure

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+).

Sources & evidence

ORD record
ord-1e611adb977c4089b4a383cb1467d368
Source dataset
uspto-grants-2008_04
Patent number
US07358273B2

Reaction notes

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