Hydrogen Bromide → 3-(4-Hydroxyphenyl)proline, ethyl ester hydrobromide

HRID 496241Notes

Reaction equation

HRID 496241 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[C:5]1(C(OCC)=O)[CH:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][CH:11]=2)[CH2:8][CH2:7][N:6]1C(=O)C)[CH3:2].[BrH:27]>CC(O)=O>[BrH:27].[OH:16][C:13]1[CH:14]=[CH:15][C:10]([CH:9]2[CH2:8][CH2:7][NH:6][C@@H:5]2[C:4]([O:3][CH2:1][CH3:2])=[O:26])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 10021599N-acetyl-2-ethoxycarbonyl-3-(4-methoxyphenyl)proline ethyl ester

Product 1

HCID 693516833-(4-Hydroxyphenyl)proline, ethyl ester hydrobromide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of N-acetyl-2-ethoxycarbonyl-3-(4-methoxyphenyl)proline ethyl ester (10 g, 27 mmol) in aqueous HBr (48%, 40 mL) and HOAc (10 mL) was heated at 120° C. under a nitrogen atmosphere overnight. The reaction mixture was concentrated in vacuo, and the residue was azeotroped with acetonitrile (2×) and Et2O/toluene (1×) to yield 3-(4-hydroxyphenyl)proline, ethyl ester hydrobromide as a mixture of diastereomers.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was azeotroped with acetonitrile (2×) and Et2O/toluene (1×)

Sources & evidence

ORD record
ord-1db09b9640994072befd5d3958045932
Source dataset
uspto-grants-2005_09
Patent number
US06943180B2

Reaction notes

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