(2-Cyclopentyloxy-5-oxo-tetrahydro-furan-3-yl)-carbamic acid allyl ester → 1-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-cyclopentyloxy-5-oxo-tetrahydro-furan-3-yl)-amide

HRID 900586Notes

Reaction equation

HRID 900586 reaction equation
C(OC(=O)NC1CC(=O)OC1OC1CCCC1)C=C.NC1C=CC(C(NC(C)C(N2CCCC2C(O)=O)=O)=O)=CC=1Cl.[O:43]=[C:44]1[O:48][CH:47]([O:49][CH2:50][CH2:51][C:52]2C=CC=[CH:54][CH:53]=2)[CH:46]([NH:58][C:59]([CH:61]2[CH2:65][CH2:64][CH2:63][N:62]2[C:66](=[O:80])[CH:67]([NH:69][C:70](=[O:79])[C:71]2[CH:76]=[CH:75][C:74]([NH2:77])=[C:73]([Cl:78])[CH:72]=2)[CH3:68])=[O:60])[CH2:45]1>>[CH:50]1([O:49][CH:47]2[CH:46]([NH:58][C:59]([CH:61]3[CH2:65][CH2:64][CH2:63][N:62]3[C:66](=[O:80])[CH:67]([NH:69][C:70](=[O:79])[C:71]3[CH:76]=[CH:75][C:74]([NH2:77])=[C:73]([Cl:78])[CH:72]=3)[CH3:68])=[O:60])[CH2:45][C:44](=[O:43])[O:48]2)[CH2:51][CH2:52][CH2:53][CH2:54]1

Participants

4

Reactant 3

HCID 18465755(2-Cyclopentyloxy-5-oxo-tetrahydro-furan-3-yl)-carbamic acid allyl esterHCID 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 229775031-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-cyclopentyloxy-5-oxo-tetrahydro-furan-3-yl)-amideYield 51%

Procedure

Prepared from (2-cyclopentyloxy-5-oxo-tetrahydro-furan-3-yl)-carbamic acid allyl ester and 97a following the method used for 98a to give the title compound (280 mg, 51% yield). 1H-NMR (500 MHz, CD3OD) δ 1.38 (d, 0.5H), 1.44 (d, 2.5H), 1.49-2.35 (m, 12H), 2.47 (dd, 0.7H), 2.56 (dd, 0.3H), 2.75 (dd, 0.3H), 2.81-2.88 (m, 0.1H), 2.97 (dd, 0.6H), 3.47-3.76 (m, 0.2H), 3.82-3.96 (m, 1H), 4.10-4.40 (m, 2H), 4.40-4.46 (m, 1H), 5.44 (d, 0.5H), 5.50 (d, 0.2H), 5.65 (d, 0.3H), 6.79 (d, 1H), 7.54-7.64 (m, 1H), 7.78 (d, 1H), 8.21-8.31 (m, 1H). Analytical HPLC 15.02, 15.34 min. LC-MS (ES+) m/e=507.3 (MH+)

Sources & evidence

ORD record
ord-4c5797dca04c4eb1af34fe45b7cb0d5d
Source dataset
uspto-grants-2008_04
Patent number
US07358273B2

Reaction notes

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