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 900584ノート

反応式

HRID 900584 の反応式
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]

参加物

4

反応物 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

生成物 1

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

実験手順

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 (175 mg, 77% yield). 1H-NMR (500 MHz, CD3OD) δ 1.13 (t, 0.5H), 1.23 (t, 2.5H), 1.36 (d, 0.5H), 1.44 (d, 2.5H), 1.75-2.38 (m, 4H), 2.56 (dd, 1H), 2.76 (dd, 1H), 3.45-3.97 (m, 5H), 4.47 (dd, 1H), 4.59-4.67 (m, 1H), 4.74 (q, 1H), 5.55 (d, 0.2H), 5.56 (d, 0.8H), 6.75-6.82 (m, 1H), 7.56 (dd, 1H), 7.77 (d, 1H), 8.39 (d, 1H). Analytical HPLC 8.17 min. LC-MS (ES+) m/e=467.4 (MH+).

出典と根拠

ORDレコード
ord-fc794c23c7a54867b8930df0afa67160
出典データセット
uspto-grants-2008_04
特許番号
US07358273B2

反応ノート

読み込み中…