(2-Cyclopentyloxy-5-oxo-tetrahydro-furan-3-yl)-carbamic acid allyl ester → (2-(4-Acetylamino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-cyclopentyloxy-5-oxo-tetrahydro-furan-3-yl)-amide

HRID 2363401Notes

Reaction equation

HRID 2363401 reaction equation
[CH2:1]([O:4]C(=O)NC1CC(=O)OC1OC1CCCC1)[CH:2]=C.[O:20]=[C:21]1[O:25][CH:24]([O:26][CH2:27][CH2:28][C:29]2C=CC=[CH:31][CH:30]=2)[CH:23]([NH:35][C:36]([CH:38]2[CH2:42][CH2:41][CH2:40][N:39]2[C:43](=[O:57])[CH:44]([NH:46][C:47](=[O:56])[C:48]2[CH:53]=[CH:52][C:51]([NH2:54])=[C:50]([Cl:55])[CH:49]=2)[CH3:45])=[O:37])[CH2:22]1>>[CH:27]1([O:26][CH:24]2[CH:23]([NH:35][C:36]([CH:38]3[CH2:42][CH2:41][CH2:40][N:39]3[C:43](=[O:57])[CH:44]([NH:46][C:47](=[O:56])[C:48]3[CH:53]=[CH:52][C:51]([NH:54][C:1](=[O:4])[CH3:2])=[C:50]([Cl:55])[CH:49]=3)[CH3:45])=[O:37])[CH2:22][C:21](=[O:20])[O:25]2)[CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

3

Reactant 2

HCID 18465755(2-Cyclopentyloxy-5-oxo-tetrahydro-furan-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 22977477(2-(4-Acetylamino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-cyclopentyloxy-5-oxo-tetrahydro-furan-3-yl)-amideYield 69%

Procedure

Prepared from 97b and (2-cyclopentyloxy-5-oxo-tetrahydro-furan-3-yl)-carbamic acid allyl ester according to the procedure used to prepare 98a to afford 215 mg of title compound (69% yield). 1H-NMR (500 MHz, 1:1 CDCl3:CD3OD) δ 1.35-1.90 (m, 1H), 1.90-2.35 (m, 4H), 2.24 (s, 3H), 2.40-3.10 (m, 2H), 3.50-3.95 (m, 3H), 4.15-4.90 (m, 3H), 5.44 (s, 0.55H), 5.56 (s, 0.15H), 5.64 (d, 0.22H), 5.71 (d, 0.08H), 7.70-8.25 (m, 3H). Analytical HPLC: 12.13 min. LC-MS (ES+): m/e=549.2 (M+H+).

Sources & evidence

ORD record
ord-9948eed25a304d0ba666b67fe7d9e98b
Source dataset
uspto-grants-2014_04
Patent number
US08691848B2

Reaction notes

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