(2-Ethoxy-5-oxo-tetrahydrofuran-3-yl)-carbamic acid allyl ester → HCID 22977481, compound

HRID 2363423Notes

Reaction equation

HRID 2363423 reaction equation
[CH2:1]([O:4]C(=O)NC1CC(=O)OC1OCC)[CH:2]=C.[O:17]=[C:18]1[O:22][CH:21]([O:23][CH2:24][CH2:25]C2C=CC=CC=2)[CH:20]([NH:32][C:33]([CH:35]2[CH2:39][CH2:38][CH2:37][N:36]2[C:40](=[O:54])[CH:41]([NH:43][C:44](=[O:53])[C:45]2[CH:50]=[CH:49][C:48]([NH2:51])=[C:47]([Cl:52])[CH:46]=2)[CH3:42])=[O:34])[CH2:19]1>>[CH2:24]([O:23][CH:21]1[CH:20]([NH:32][C:33]([CH:35]2[CH2:39][CH2:38][CH2:37][N:36]2[C:40](=[O:54])[CH:41]([NH:43][C:44](=[O:53])[C:45]2[CH:50]=[CH:49][C:48]([NH:51][C:1](=[O:4])[CH3:2])=[C:47]([Cl:52])[CH:46]=2)[CH3:42])=[O:34])[CH2:19][C:18](=[O:17])[O:22]1)[CH3:25]

Participants

3

Reactant 2

HCID 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 22977481HCID 22977481, compound

Procedure

Prepared from (2-ethoxy-5-oxo-tetrahydro-furan-3-yl)-carbamic acid allyl ester and 97b following the method used for 98a. The title compound was isolated as a white solid (51 mg, 18% yield). 1H-NMR (500 MHz, 1:1 CDCl3:CD3OD) δ 1.08-1.35 (m, 3H), 1.35-1.55 (m, 3H), 1.75-2.44 (m, 4H), 2.26 (s, 3H), 2.44-3.07 (m, 2H), 3.48-3.97 (m, 2H), 4.18-4.92 (m, 5H), 5.32 (d, 0.4H), 5.47 (d, 0.1H), 5.58 (d, 0.4H), 5.64 (d, 0.1H), 7.70-8.35 (m, 3H). Analytical HPLC 10.37, 10.54 min. LC-MS (ES+) m/e=509.2 (M+H+).

Sources & evidence

ORD record
ord-a19191e704c94231a7cc379b0a614696
Source dataset
uspto-grants-2014_04
Patent number
US08691848B2

Reaction notes

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