(2-Ethoxy-5-oxo-tetrahydrofuran-3-yl)-carbamic acid allyl ester → HCID 22977791, compound

HRID 900628Notes

Reaction equation

C(OC(=O)NC1CC(=O)OC1OCC)C=C.[C:17]([O:21][C:22](=[O:50])[NH:23][CH:24]([CH3:49])[C:25]([N:27]1[CH2:31][CH2:30][CH2:29][CH:28]1[C:32](=[O:48])[NH:33][CH:34]1[CH2:38][C:37](=[O:39])[O:36][CH:35]1[O:40][CH2:41][C:42]1C=CC=CC=1)=[O:26])([CH3:20])([CH3:19])[CH3:18]>>[C:17]([O:21][C:22](=[O:50])[NH:23][CH:24]([CH3:49])[C:25]([N:27]1[CH2:31][CH2:30][CH2:29][CH:28]1[C:32](=[O:48])[NH:33][CH:34]1[CH2:38][C:37](=[O:39])[O:36][CH:35]1[O:40][CH2:41][CH3:42])=[O:26])([CH3:19])([CH3:18])[CH3:20]

Participants

Reactant 2

HCID 22149038(2-Ethoxy-5-oxo-tetrahydrofuran-3-yl)-carbamic acid allyl ester

HCID 22977790{2-[2-(2-Benzyloxy-5-oxo-tetrahydro-furan-3-ylcarbamoyl)-pyrrolidin-1-yl]-1-methyl-2-oxo-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 22977791HCID 22977791, compoundYield 73%

Procedure

Prepared from (2-ethoxy-5-oxo-tetrahydro-furan-3-yl) carbamic acid allyl ester 74 following the method used in the synthesis of 75 to give the title compound as a pale yellow solid (660 mg, 73% yield). 1H-NMR (500 MHz, CD3OD) δ 1.14-1.36 (m, 6H), 1.42 (s, 9H), 1.75-2.29 (m, 4H), 2.48 (dd, 0.5H), 2.58 (dd, 0.5H), 2.72-2.85 (m, 0.5H), 2.99 (dd, 0.5H), 3.43-3.91 (m, 4H), 4.07-4.52 (m, 2.5H), 4.53-4.72 (m, 0.5H), 5.37 (s, 0.5H), 5.57 (d, 0.5H). Analytical HPLC (mixture of 2 diastereomers) 7.92, 8.14 min. LC-MS (ES+) m/e=414.3 (MH+).

Sources & evidence

ORD record: ord-22f168a8419740c18ee61eb4ab404960
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07358273B2

Reaction notes

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