Sulfuric Acid → L-Hydroxyproline

HRID 1950704Notes

Reaction equation

HRID 1950704 reaction equation
[B:1]([OH:4])([OH:3])[OH:2].[Cl-].[K+].[OH-].[K+].[CH3:9][C:10]1[CH:11]=[CH:12][C:13]([S:16]([NH:19][Cl:20])(=[O:18])=[O:17])=[CH:14][CH:15]=1.[CH3:21][N:22]([CH3:31])[C:23]1[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][CH:24]=1.S(=O)(=O)(O)[OH:33].O[N:38]1[CH2:45][CH2:44][CH2:43][C@H:39]1[C:40]([OH:42])=[O:41]>O.COCCO.C(O)C>[B:1]([OH:4])([OH:3])[OH:2].[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([NH:19][Cl:20])(=[O:18])=[O:17])=[CH:12][CH:11]=1.[CH3:21][N:22]([CH3:31])[C:23]1[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][CH:24]=1.[NH:38]1[CH2:45][C@H:44]([OH:33])[CH2:43][C@H:39]1[C:40]([OH:42])=[O:41]

Participants

14

Reactant 7

HCID 1118Sulfuric AcidHCID 4873Potassium ChlorideHCID 74794-(Dimethylamino)BenzaldehydeHCID 7628Boric AcidHCID 14797Potassium HydroxideHCID 31388TosylchloramideHCID 22795248L-Proline, 1-hydroxy

Product 4

HCID 5810L-HydroxyprolineHCID 74794-(Dimethylamino)BenzaldehydeHCID 7628Boric AcidHCID 31388Tosylchloramide

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×HCID 80192-MethoxyethanolSolvent

Procedure

A boric acid buffer was prepared by dissolving 6.18 g of boric acid and 22.5 g of KCl in distilled water, adjusting at pH 8.7 with potassium hydroxide and making the total volume 100 ml. A chloramine T solution was prepared by dissolving 1.41 g of chloramine T (NACALAITESQUE, Catalog No.080-05) in 25 ml of 2-methoxyethanol (NACALAITESQUE, Catalog No.153-10). A p-dimethylaminobenzaldehyde solution was prepared by dissolving 12 g of p-dimethylaminobenzaldehyde (NACALAITESQUE, Catalog No.128-16) in 20 ml of ethanol followed by adding a mixture of 2.74 ml of concentrated sulfuric acid and 20 ml of ethanol slowly to the solution with cooling on ice. A hydroxyproline conventional solution was prepared by dissolving 3 mg of hydroxy-L-proline (NACALAITESQUE, Catalog No.188-17) in 1 ml of distilled water (3 mg/ml).

Workup

  1. additionby adding
  2. temperaturewith cooling on ice

Sources & evidence

ORD record
ord-71abd08380f64e7f8f88462895fd8297
Source dataset
uspto-grants-2013_03
Patent number
US08404652B2

Reaction notes

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