L-Hydroxyproline → HCID 3677107, compound

HRID 398332Notes

Reaction equation

HRID 398332 reaction equation
[OH:1][C@H:2]1[CH2:6][NH:5][C@H:4]([C:7]([OH:9])=[O:8])[CH2:3]1.[CH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][C:11]=1[S:20](Cl)(=[O:22])=[O:21]>O.C([O-])([O-])=O.[Na+].[Na+]>[OH:1][CH:2]1[CH2:6][N:5]([S:20]([C:11]2[CH:12]=[CH:13][C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:10]=2)(=[O:22])=[O:21])[CH:4]([C:7]([OH:9])=[O:8])[CH2:3]1

Participants

5

Reactant 2

HCID 5810L-HydroxyprolineHCID 71252-Naphthalenesulfonyl chloride

Product 1

HCID 3677107HCID 3677107, compoundYield 63.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10340Sodium CarbonateSolvent

Procedure

2.62 g of (2S,4R)-4-hydroxyproline are dissolved in 15 ml of water containing 5.9 g of Na2CO3 and 5.21 g of 2-naphthalenesulphonyl chloride are added. After vigorous stirring for 18 hours at RT, the mixture is drained and the filtrate is then acidified to pH=1. The resulting mixture is again drained, washed with water and dried in order to obtain 4.1 g of the expected compound.

Workup

  1. additionare added
  2. washwashed with water
  3. customdried in order

Sources & evidence

ORD record
ord-fa32b7dee57b4cd4b9ccc31f1b8463b6
Source dataset
uspto-grants-2003_08
Patent number
US06610882B2

Reaction notes

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