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 1861268Notes

Reaction equation

HRID 1861268 reaction equation
C(OC(=O)NC1CC(=O)OC1OCC)C=C.NC1C=CC(C(NC(C)C(N2CCCC2C(O)=O)=O)=O)=CC=1Cl.[O:40]=[C:41]1[O:45][CH:44]([O:46][CH2:47][CH2:48]C2C=CC=CC=2)[CH:43]([NH:55][C:56]([CH:58]2[CH2:62][CH2:61][CH2:60][N:59]2[C:63](=[O:77])[CH:64]([NH:66][C:67](=[O:76])[C:68]2[CH:73]=[CH:72][C:71]([NH2:74])=[C:70]([Cl:75])[CH:69]=2)[CH3:65])=[O:57])[CH2:42]1>>[CH2:47]([O:46][CH:44]1[CH:43]([NH:55][C:56]([CH:58]2[CH2:62][CH2:61][CH2:60][N:59]2[C:63](=[O:77])[CH:64]([NH:66][C:67](=[O:76])[C:68]2[CH:73]=[CH:72][C:71]([NH2:74])=[C:70]([Cl:75])[CH:69]=2)[CH3:65])=[O:57])[CH2:42][C:41](=[O:40])[O:45]1)[CH3:48]

Participants

4

Reactant 3

HCID 186236851-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acidHCID 22149038(2-Ethoxy-5-oxo-tetrahydrofuran-3-yl)-carbamic acid allyl esterHCID 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)-amide

Procedure

Prepared from (2-ethoxy-5-oxo-tetrahydro-furan-3-yl)-carbamic acid allyl ester and 97a following the method used for 98a. The title compound was isolated as a white solid (195 mg, 82% yield). 1H-NMR (500 MHz, CD3OD) δ 1.32-1.55 (m, 3H), 1.58-1.77 (m, 3H), 1.98-2.54 (m, 4H), 2.68-2.76 (d, 0.3H), 2.79-2.89 (m, 0.7H), 2.96-3.10 (m, 0.7H), 3.18-3.27 (dd, 0.3H), 3.72-4.18 (m, 4H), 4.46-5.12 (m, 3H), 5.60 (s, 0.4H), 5.74-5.84 (m, 0.6H), 7.03 (d, 0.8H), 7.75-7.86 (m, 1H), 8.01 (d, 0.7H), 8.35 (d, 0.3H), 8.74 (d, 0.2H). Analytical HPLC 8.31 min. LC-MS (ES+) m/e=467.3 (MH+).

Sources & evidence

ORD record
ord-0fa1e7268d2f4b159dd01215f49b8a28
Source dataset
uspto-grants-2003_03
Patent number
US06531474B1

Reaction notes

Loading…