Ethyl bromoacetate → (S)-3-chloro-N-(4-hydroxy-1-(4-(1-methyl-2-(2-methyl-1,3-dioxolan-2-yl)-1H-imidazol-4-yl)phenyl)butan-2-yl)-4-isopropoxybenzamide

HRID 1436205Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][C:31]=1[O:32][CH:33]([CH3:35])[CH3:34])[C:5]([NH:7][C@H:8]([CH2:26][CH2:27][OH:28])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:17]=[C:18]([C:22](=NO)[CH3:23])[N:19]([CH3:21])[CH:20]=2)=[CH:12][CH:11]=1)=[O:6].[C:36]([O-:39])([O-])=O.[K+].[K+].BrC[C:44](OCC)=[O:45]>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][C:31]=1[O:32][CH:33]([CH3:34])[CH3:35])[C:5]([NH:7][C@H:8]([CH2:26][CH2:27][OH:28])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:17]=[C:18]([C:22]3([CH3:23])[O:39][CH2:36][CH2:44][O:45]3)[N:19]([CH3:21])[CH:20]=2)=[CH:12][CH:11]=1)=[O:6]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of compound 3 (2.66 g, 7.27 mmol) in DMF (15 mL) was added K2CO3 (2.00 g, 15 mmol) and ethyl bromoacetate (1.61 mL, 14.5 mmol). The resulting mixture was stirred at 60° C. for three hours. The mixture was diluted with water and extracted with EtOAc (3×50 mL). The organic layers were combined, dried over Na2SO4, and concentrated. Purification with column chromatography (Hexanes/EtOAc 50:50) gave the product 4 (3.02 g, 91%).

Workup

extractionextracted with EtOAc (3×50 mL)
dry with materialdried over Na2SO4
concentrationconcentrated
customPurification with column chromatography (Hexanes/EtOAc 50:50)

Sources & evidence

ORD record: ord-e563ddcf23c24d3ca4199467586442fb
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07618981B2

Reaction notes

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