L-Hydroxyproline → HCID 69945184, compound

HRID 1870950Notes

Reaction equation

HRID 1870950 reaction equation
[OH:1][C@H:2]1[CH2:6][NH:5][C@H:4]([C:7](O)=O)[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].[C:24]([O-:27])([O-])=[O:25].[Na+].[Na+]>O>[CH2:15]([O:1][C@H: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])[C@H:4]([CH2:7][C:24]([OH:27])=[O:25])[CH2:3]1)[C:14]1[CH:19]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 5810L-HydroxyprolineHCID 71252-Naphthalenesulfonyl chlorideHCID 10340Sodium Carbonate

Product 1

HCID 69945184HCID 69945184, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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-a538797cab2c48d38ab8640ab1ed5b37
Source dataset
uspto-grants-2000_08
Patent number
US06100278

Reaction notes

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