2-Bromo-1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-one → [4-((2R,3R)-1-(4-fluorophenyl)-4-oxo-3-{[2-oxo-2-(5,6,7,8-tetrahydronaphthalen-2-yl)ethyl]thio}azetidin-2-yl)phenoxy]acetic acid

HRID 1366319Notes

Reaction equation

HRID 1366319 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10](=[O:36])[CH2:11][S:12][C@H:13]3[C:16](=[O:17])[N:15]([C:18]4[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=4)[C@@H:14]3[C:25]3[CH:35]=[CH:34][C:28]([O:29][CH2:30][C:31]([OH:33])=[O:32])=[CH:27][CH:26]=3)=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.Br[CH2:38]C(C1C=CC2CCCCC=2C=1)=O>>[F:24][C:21]1[CH:20]=[CH:19][C:18]([N:15]2[C:16](=[O:17])[C@H:13]([S:12][CH2:11][C:10](=[O:36])[C:6]3[CH:7]=[CH:8][C:9]4[CH2:38][CH2:1][CH2:2][CH2:3][C:4]=4[CH:5]=3)[C@H:14]2[C:25]2[CH:35]=[CH:34][C:28]([O:29][CH2:30][C:31]([OH:33])=[O:32])=[CH:27][CH:26]=2)=[CH:23][CH:22]=1

Participants

3

Reactant 2

HCID 73539912-Bromo-1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-oneHCID 66934629{4-[(2R,3R)-3-{[2-(2,3-dihydro-1H-inden-5-yl)-2-oxoethyl]thio}-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetic acid

Product 1

HCID 66934516[4-((2R,3R)-1-(4-fluorophenyl)-4-oxo-3-{[2-oxo-2-(5,6,7,8-tetrahydronaphthalen-2-yl)ethyl]thio}azetidin-2-yl)phenoxy]acetic acid

Procedure

The titled compound above was prepared using the same procedure as that used for the synthesis of {4-[(2R,3R)-3-{[2-(2,3-dihydro-1H-inden-5-yl)-2-oxoethyl]thio}-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetic acid but using 2-bromo-1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethanone instead of 2-bromo-1-(2,3-dihydro-1H-inden-5-yl)ethanone. 1H NMR [(CD3)2SO), 400 MHz]δ 1.66-1.75 (m, 4H), 2.66-2.77 (m, 4H), 4.22-4.31 (m, 3H), 4.62 (s, 2H), 5.11 (d, 1H), 6.86-7.61 (m, 11H).

Sources & evidence

ORD record
ord-6199f4e9be6140749f24b6670779b555
Source dataset
uspto-grants-2011_02
Patent number
US07893048B2

Reaction notes

Loading…