1-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid → 1-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-ethoxy-5-oxo-tetrahydro-furan-3-yl)-amide

HRID 900591Notes

Reaction equation

HRID 900591 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]C2C=CC=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>>[CH2:31]([O:30][CH:28]1[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][C:25](=[O:24])[O:29]1)[CH3:32]

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 229775061-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-ethoxy-5-oxo-tetrahydro-furan-3-yl)-amideYield 59%

Procedure

Prepared from anti-(2-ethoxy-5-oxo-tetrahydro-furan-3-yl)-carbamic acid allyl ester and 97a following the method used for 98a to afford 175 mg of title compound (59%). 1H-NMR (500 MHz, 1:1 CDCl3:CD3OD) δ 1.10-1.28 (m, 3H), 1.42 (d, 0.6H), 1.46 (d, 2.4H), 1.75-2.45 (m, 4H), 2.45-2.70 (m, 1H), 2.80-3.05 (m, 1H), 3.50-3.95 (m, 4H), 4.20-4.75 (m, 3H), 4.75-4.90 (m, 1H), 5.32 (s, 0.8H), 5.38 (s, 0.2H), 6.80 (d, 1H), 7.55-7.84 (m, 2H). Analytical HPLC: 10.47 min. LC-MS (ES+): m/e=467.3 (M+H+).

Sources & evidence

ORD record
ord-ad8a9fb7c88043b0a66830aebc863f5b
Source dataset
uspto-grants-2008_04
Patent number
US07358273B2

Reaction notes

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