Furan → HCID 86672887, compound

HRID 1752837Notes

Reaction equation

HRID 1752837 reaction equation
Br[CH:2]([CH2:14][CH3:15])[C:3]([NH:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].[O:16]1[CH:20]=[CH:19][CH:18]=[CH:17]1.[C:21](OCC)(=O)C>>[CH2:14]([C@H:2]1[C@@H:21]2[C:20](=[O:16])[C@H:19]([CH:18]=[CH:17]2)[N:5]([O:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:3]1=[O:4])[CH3:15]

Participants

4

Reactant 3

HCID 8029FuranHCID 8857Ethyl Acetate2×HCID 64974143HCID 64974143, compound

Product 1

HCID 86672887HCID 86672887, compoundYield 86%

Procedure

Prepared in 86% yield (40.6 mg, 0.157 mmol) from the reaction of 2-bromo-N-(phenylmethoxy)butanamide (50.0 mg, 0.183 mmol) with furan via general procedure B. Rf=0.3 (3:1, hexanes:EtOAc); Rf 0.50 (3:1, hexanes:ethyl acetate); 1H-NMR (500 MHz, CDCl3): δ 7.45-7.42 (m, 2H), 7.41-7.32 (m, 3H), 6.51 (dd, J=6.0, 1 Hz, 1H), 6.38 (dd, J=6.0, 1.8 Hz, 1H), 5.25 (d, J=1.2 Hz, 1H), 4.99 (d, J=11.0 Hz, 1H), 4.95 (dd, J=5.1, 1.8 Hz, 1H), 4.87 (d, J=11.0 Hz, 1H), 2.99 (dt, J=10.1, 5.1 Hz, 1H), 2.07-1.96 (dqd, J=15.4, 7.5 5.3, 7.5, 15.4 Hz, 1H), 1.24-1.14 (m, 1H), and 1.03 (t, J=7.5 Hz, 3H). 13C-NMR (126 MHz, CDCl3): δ 172.1, 135.8, 133.6, 129.7, 128.8, 128.6, 91.4, 91.4, 81.3, 78.0, 51.8, 19.5, and 12.3; IR (film) 3250 (br), 3032, 2966, 2929, 2877, 1696, 1497, 1455, 1371, 1209, 1104, 1055, 1033 cm-1; HR-ESIMS calculated for C15H17NNaO3 (M+Na)+282.1101; observed 282.1083.

Sources & evidence

ORD record
ord-e7d68549f85f4bec9564eeeddfe412fd
Source dataset
uspto-grants-2015_10
Patent number
US09163033B2

Reaction notes

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