4-Hydroxyphenylboronic acid → HCID 59643927, compound

HRID 2252438Notes

Reaction equation

HRID 2252438 reaction equation
Br[C:2]1[S:6][C:5]([C@H:7]2[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:9](=[O:17])[C@@H:8]2[CH2:18][CH2:19][C@@H:20]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[OH:21])=[CH:4][CH:3]=1.[OH:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1>>[F:28][C:25]1[CH:26]=[CH:27][C:22]([C@@H:20]([OH:21])[CH2:19][CH2:18][C@@H:8]2[C@@H:7]([C:5]3[S:6][C:2]([C:33]4[CH:34]=[CH:35][C:30]([OH:29])=[CH:31][CH:32]=4)=[CH:3][CH:4]=3)[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:9]2=[O:17])=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 27343604-Hydroxyphenylboronic acidHCID 59643918HCID 59643918, compound

Product 1

HCID 59643927HCID 59643927, compoundYield 56.5%

Procedure

(3R,4S)-4-(5-Bromo-2-thienyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-1-phenylazetidin-2-one (69.8 mg, 0.152 mmol) was coupled with 4-hydroxyphenyl boronic acid (25.2 mg, 0.183 mmol) under standard Suzuki conditions illustrated by Example 42. Purification by chromatography (12 g silica gel, 15% to 100% ethyl acetate-hexane) afforded (3R,4S)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-[5-(4-hydroxyphenyl)-2-thienyl]-1-phenylazetidin-2-one (40.7 mg, 56% yield) as a clear foam; Rf 0.39 (1:1 ethyl acetate-hexane); 1H NMR (300 MHz, CDCl3) δ 7.64-7.60 (m, 4H), 7.56-7.48 (m, 5H), 7.33-7.27 (m, 2H), 7.25-7.20 (m, 2H), 7.07 (d, J=8.6 Hz, 2H), 6.81 (br s, 1H), 5.14 (d, J=2.3 Hz, 1H), 5.00-4.95 (m, 1H), 3.57-3.50 (m, 1H), 2.29-2.11 (m, 4H) ppm; MS [M+H]+ 474.0.

Workup

  1. customPurification by chromatography (12 g silica gel, 15% to 100% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-53df627a37604821917f5a91f98c480f
Source dataset
uspto-grants-2008_01
Patent number
US07320972B2

Reaction notes

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