Phenylboronic Acid → HCID 86628194, compound

HRID 420399Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:46])[CH:5]([O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH2:39][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[C:19]([C:21]2[C:22](=[O:30])[N:23]([CH3:29])[C:24](=[O:28])[N:25]([CH3:27])[CH:26]=2)[CH:18]=[C:17](Br)[CH:16]=1)[CH3:7])[CH3:2].[C:47]1(B(O)O)[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>>[CH2:1]([O:3][C:4](=[O:46])[CH:5]([O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH2:39][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH:18]=[C:19]([C:21]2[C:22](=[O:30])[N:23]([CH3:29])[C:24](=[O:28])[N:25]([CH3:27])[CH:26]=2)[CH:20]=1)[CH3:7])[CH3:2]

Participants

Reactant 2

HCID 66827Phenylboronic Acid

HCID 68746208HCID 68746208, compound

Product 1

HCID 86628194HCID 86628194, compoundYield 30%

Procedure

A similar procedure as described in Example 1, step 2 was used, starting from 4-[3-{6-[3-bromo-5-(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-phenoxy]-hexyl}-(2-(2-ethoxycarbonyl-ethyl)-phenoxy)-butyric acid ethyl ester (27 mg, 0.04 mmol) and phenylboronic acid (23 mg, 0.19 mmol) to obtain 4-[3-{6-[5-(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-biphenyl-3-yloxy]-hexyl}-(2-(2-ethoxycarbonyl-ethyl)-phenoxy)-butyric acid ethyl ester (8 mg, 30%) as a light yellow oil: ES(+)-LRMS m/e calculated for C41H50N2O8 (M+H)+ 699.6, found 699.4.

Sources & evidence

ORD record: ord-b6f26d8c332e4821bbbaa60d790dfb05
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093385B2

Reaction notes

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