Hydrogen Bromide → 2-(3-hydroxyphenylaminocarbonyl)-L-proline hydrobromide

HRID 23595Notes

Reaction equation

HRID 23595 reaction equation
C([N:11]1[CH2:18][CH2:17][CH2:16][C@@:12]1([C:19]([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([OH:28])[CH:23]=1)=[O:20])[C:13]([OH:15])=[O:14])(OCC1C=CC=CC=1)=O.[BrH:29]>CC(O)=O>[BrH:29].[OH:28][C:24]1[CH:23]=[C:22]([NH:21][C:19]([C@@:12]2([C:13]([OH:15])=[O:14])[CH2:16][CH2:17][CH2:18][NH:11]2)=[O:20])[CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 20757882N-Cbz-[2-(3-hydroxyphenylaminocarbonyl)]-L-proline

Product 1

HCID 697683902-(3-hydroxyphenylaminocarbonyl)-L-proline hydrobromideYield 70%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To N-Cbz-[2-(3-hydroxyphenylaminocarbonyl)]-L-proline (5.0 mmol) in HOAc (10 mL) was added 30% HBr in acetic acid and the solution stirred for 40 min. The reaction was quenched by addition of 100 mL ethylether, and the resulting precipitate collected and recrystalized from MeOH/Et2O to afford 3.5 mmol 2-(3-hydroxyphenylaminocarbonyl)-L-proline hydrobromide (70%)

Workup

  1. customThe reaction was quenched by addition of 100 mL ethylether
  2. customthe resulting precipitate collected
  3. customrecrystalized from MeOH/Et2O

Sources & evidence

ORD record
ord-9bb638b89e484910aa33f3ac3768b197
Source dataset
uspto-grants-2005_02
Patent number
US06852752B2

Reaction notes

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