Acetic Acid → 6-(((1-(2-(tert-butoxy)-2-oxoethyl)-1H-imidazol-2-yl)methyl)(4-(prop-2-yn-1-yloxy)benzyl)amino)hexanoic acid

HRID 1052319Notes

Reaction equation

[CH2:1]([O:4][C:5]1[CH:20]=[CH:19][C:8]([CH2:9][NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:7][CH:6]=1)[C:2]#[CH:3].[CH:21]([C:23]1[N:24]([CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH:25]=[CH:26][N:27]=1)=O.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl.CO.O>[C:32]([O:31][C:29](=[O:30])[CH2:28][N:24]1[CH:25]=[CH:26][N:27]=[C:23]1[CH2:21][N:10]([CH2:9][C:8]1[CH:19]=[CH:20][C:5]([O:4][CH2:1][C:2]#[CH:3])=[CH:6][CH:7]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])([CH3:35])([CH3:34])[CH3:33]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 6-((4-(prop-2-yn-1-yloxy)benzyl)amino)hexanoic acid (0.4125 g, 1.50 mmol), tert-butyl 2-(2-formyl-1H-imidazol-1-yl)acetate (0.315 g, 1.50 mmol) and AcOH (0.05 mL) in DCE (40 mL) at 0° C. was treated with NaBH(OAc)3 (0.636 g, 3.0 mmol). The reaction mixture was stirred at 0° C. for 30 min and at room temperature for overnight and decomposed with water and methanol. The reaction mixture was concentrated under reduced pressure to give a residue, which was purified by Biotage SP4 over silica gel to afford 6-(((1-(2-(tert-butoxy)-2-oxoethyl)-1H-imidazol-2-yl)methyl)(4-(prop-2-yn-1-yloxy)benzyl)amino)hexanoic acid (0.268 g, 38%). MS (ESI), 470.3 (M+H)+.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customto give a residue, which
customwas purified by Biotage SP4 over silica gel

Sources & evidence

ORD record: ord-77852c13c55946a69e949d788d91621f
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388144B2

Reaction notes

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