tert-butyl N-(2-hydroxyethyl)carbamate → HCID 69345211, compound

HRID 1948232Notes

Reaction equation

HRID 1948232 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)[CH:10]=[CH:9][C:8]2=[O:20])=[C:4]([F:23])[CH:3]=1.O[CH2:25][CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31]>>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:8](=[O:20])[CH:9]=[CH:10][C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:25][CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:15][CH:14]=3)=[CH:12]2)=[C:4]([F:23])[CH:3]=1

Participants

3

Reactant 2

HCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 69345556HCID 69345556, compound

Product 1

HCID 69345211HCID 69345211, compoundYield 66.7%

Procedure

The title compound was prepared from 1-(4-chloro-2-fluorobenzyl)-5-(4-hydroxyphenyl)pyridin-2(1H)-one (1 eq, 0.60 mmol, 0.20 g, Example 20 Step 2) and tert-butyl 2-hydroxyethylcarbamate (1.5 eq, 0.90 mmol, 0.10 g) according to the procedure described for Example 25 Step 2. The crude product was purified by crystallization in pentane/Et2O followed by silica gel chromatography (AIT Flashsmart prepacked column 25 g SiO2, CH2Cl2/AcOEt 80/20) to afford tert-butyl 2-(4-(1-(4-chloro-2-fluorobenzyl)-6-oxo-1,6-dihydropyridin-3-yl)phenoxy)ethylcarbamate (0.40 mmol, 0.19 g, 66%) as a yellow oil.

Workup

  1. customThe crude product was purified by crystallization in pentane/Et2O

Sources & evidence

ORD record
ord-2fcf37d231424cfd86cf36f6e44cab77
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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