Ether hydrochloride → 3-Oxo-3-(3-pyrimidin-2-yl-phenyl)-propionic acid tert-butyl ester

HRID 498243Notes

Reaction equation

HRID 498243 reaction equation
CO[C:3](=[O:16])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:5]=1.N1C=CC=NC=1C1C=C(C=CC=1)C(O)=O.Cl.CCOCC.[C:38]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])(=[O:40])[CH3:39].[Li]>CO>[C:42]([O:41][C:38](=[O:40])[CH2:39][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:11]=[CH:12][CH:13]=[CH:14][N:15]=2)[CH:5]=1)([CH3:45])([CH3:44])[CH3:43]

Participants

6

Reactant 4

HCID 10953452Ether hydrochlorideHCID 223173733-(Pyrimidin-2-yl)benzoic acidHCID 69487031Methyl 3-(pyrimidin-2-YL)benzoateHCID 86586795Lithium Tert-butyl Acetate

Product 1

HCID 694873573-Oxo-3-(3-pyrimidin-2-yl-phenyl)-propionic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared from 3-pyrimidin-2-yl-benzoic acid methyl ester [prepared by the following procedure: 3-Pyrimidin-2-yl-benzoic acid (3.0 g) was esterified by heating in MeOH (160 ml)/4N HCl-Et2O (40 ml) for 16 h at 40° C.; white crystals (1.99 g).] (1.99 g, 9.3 mmol) by treatment with lithium tert-butyl acetate according to general procedure K (method b). Obtained as a light yellow oil (3.24 g, crude product).

Workup

  1. customprepared by the following procedure
  2. customObtained as a light yellow oil (3.24 g, crude product)

Sources & evidence

ORD record
ord-18004619311a4f279e25fd3a56f7e827
Source dataset
uspto-grants-2005_09
Patent number
US06949542B2

Reaction notes

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