1-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid → HCID 22977504, compound

HRID 2363403Notes

Reaction equation

HRID 2363403 reaction equation
NC1C=CC(C(NC(C)C(N2CCCC2C(O)=O)=O)=O)=CC=1Cl.[O:24]=[C:25]1[O:29][CH:28]([O:30][CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=CC=2)[CH:27]([NH:39][C:40]([CH:42]2[CH2:46][CH2:45][CH2:44][N:43]2[C:47](=[O:61])[CH:48]([NH:50][C:51](=[O:60])[C:52]2[CH:57]=[CH:56][C:55]([NH2:58])=[C:54]([Cl:59])[CH:53]=2)[CH3:49])=[O:41])[CH2:26]1>>[CH:32]1([CH2:31][O:30][CH:28]2[CH:27]([NH:39][C:40]([CH:42]3[CH2:46][CH2:45][CH2:44][N:43]3[C:47](=[O:61])[CH:48]([NH:50][C:51](=[O:60])[C:52]3[CH:57]=[CH:56][C:55]([NH2:58])=[C:54]([Cl:59])[CH:53]=3)[CH3:49])=[O:41])[CH2:26][C:25](=[O:24])[O:29]2)[CH2:33][CH2:38][CH2:37][CH2:36]1

Participants

3

Reactant 2

HCID 186236851-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acidHCID 229775121-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (5-oxo-2-phenethyloxy-tetrahydro-furan-3-yl)-amide

Product 1

HCID 22977504HCID 22977504, compoundYield 51%

Procedure

Prepared from 97a and syn-(2-cyclopentylmethoxy-5-oxo-tetrahydro-furan-3-yl)-carbamic acid allyl ester according to the procedure used to prepare 98a to afford 195 mg of title compound (51% yield). 1H-NMR (500 MHz, 1:1 CDCl3:CD3OD) δ 1.15-1.90 (m, 1H), 1.90-2.40 (m, 5H), 2.55-2.78 (m, 2H), 3.50-3.90 (m, 4H), 4.38-4.92 (m, 3H), 5.53 (d, 0.8H), 5.57 (d, 0.2H), 6.78 (d, 1H), 7.50-8.15 (m, 2H). Analytical HPLC: 10.48 min. LC-MS (ES+): m/e=521.2 (M+H+).

Sources & evidence

ORD record
ord-1d11ebcbb93a4f18ae4fa6a70bdf0a39
Source dataset
uspto-grants-2014_04
Patent number
US08691848B2

Reaction notes

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