4-Hydroxyphenylboronic acid → HCID 59643908, compound

HRID 2252435Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C@H:8]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[C:10](=[O:19])[C@@H:9]2[CH2:20][CH2:21][C@@H:22]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[OH:23])[CH:5]=[CH:6][CH:7]=1.[OH:31][C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1>>[F:18][C:15]1[CH:16]=[CH:17][C:12]([N:11]2[C@H:8]([C:4]3[CH:3]=[C:2]([C:35]4[CH:36]=[CH:37][C:32]([OH:31])=[CH:33][CH:34]=4)[CH:7]=[CH:6][CH:5]=3)[C@@H:9]([CH2:20][CH2:21][C@@H:22]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[OH:23])[C:10]2=[O:19])=[CH:13][CH:14]=1

Participants

Reactant 2

HCID 27343604-Hydroxyphenylboronic acid

HCID 59643931HCID 59643931, compound

Product 1

HCID 59643908HCID 59643908, compoundYield 63%

Procedure

(3R,4S)-4-(3-Bromophenyl)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]azetidin-2-one (42 mg, 0.089 mmol) was coupled with 4-hydroxyphenyl boronic acid (18 mg, 0.13 mmol) under standard Suzuki conditions illustrated by Example 42. Purified by chromatography (silica gel, 10% to 90% ethyl acetate-hexane) to afford (3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4′-hydroxybiphenyl-3-yl)azetidin-2-one (27 mg, 63% yield); Rf 0.31 (1:1 ethyl acetate-hexane); 1H NMR (300 MHz, CDCl3) δ 7.54-7.37 (m, 6H), 7.32-7.22 (m, 4H), 7.04-6.87 (m, 6H), 5.24 (br s, 1H), 4.72 (t, J=6.0 Hz, 1H), 4.67 (d, J=2.4 Hz, 1H), 3.17 (ddd, J=5.3, 2.5, 2.4 Hz, 1H), 2.26 (br s, 1H), 2.09-1.88 (m, 4H) ppm.

Workup

customPurified by chromatography (silica gel, 10% to 90% ethyl acetate-hexane)

Sources & evidence

ORD record: ord-1e2d1cc56ad24ba0ac7bf928546a3380
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07320972B2

Reaction notes

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