L-Hydroxyproline → HCID 28374363, compound

HRID 1785370Notes

Reaction equation

HRID 1785370 reaction equation
[NH:1]1[CH2:9][C@H:7]([OH:8])[CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]=[C:18]=[O:19])=[CH:13][CH:12]=1>[OH-].[Na+]>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([N:1]2[CH2:9][C@H:7]([OH:8])[CH2:6][C@H:2]2[C:3]([OH:5])=[O:4])=[O:19])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 5810L-HydroxyprolineHCID 76934-Chlorophenyl Isocyanate

Product 1

HCID 28374363HCID 28374363, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
-1 °C

Procedure

9.4 g (71.685 mmol) of L-hydroxyproline are dissolved in 71.68 ml of NaOH solution (c=1 mol/l) at from −2 to 0° C., a solution of 11.008 g (71.685 mmol) of 4-chlorophenyl isocyanate in 70 ml of IBMK is subsequently added, and the mixture is stirred at −1° C. for 1 hour. Conventional work-up gives 18.52 g of (2S,4R)-1-(4-chlorophenyl-carbamoyl)-4-hydroxypyrrolidine-2-carboxylic acid;

Sources & evidence

ORD record
ord-6ab9d34cdbdb4a8fa75fc75df7f3247b
Source dataset
uspto-grants-2009_03
Patent number
US07504500B2

Reaction notes

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