Pyridine → HCID 355961, compound

HRID 1503181Notes

Reaction equation

HRID 1503181 reaction equation
[NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][SH:4].O=[CH:9][C@@H:10]([C@H:12]([C@H:14]([C@@H:16]([CH2:18][OH:19])[OH:17])[OH:15])[OH:13])[OH:11].N1C=CC=CC=1>O>[OH:11][CH:10]([CH:9]1[NH:1][CH:2]([C:5]([OH:7])=[O:6])[CH2:3][S:4]1)[CH:12]([OH:13])[CH:14]([OH:15])[CH:16]([OH:17])[CH2:18][OH:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 5862L-(+)-CysteineHCID 3037556(2R,3S,4S,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 355961HCID 355961, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

Under an argon atmosphere, L-cysteine (2.42 g, 20.0 mmol), D-galactose (3.60 g, 20.0 mmol), and pyridine (0.40 ml, 5.0 mmol) were added to water (340 ml), and the solution was heated at 65° C. for 1 hour, and left standing at room temperature for 2 hours. The precipitated solid was collected by filtration, and dried under reduced pressure to give 2-(1,2,3,4,5-pentahydroxypentyl)thiazolidine-4-carboxylic acid (4.70 g) as white crystals.

Workup

  1. waitleft
  2. filtrationThe precipitated solid was collected by filtration
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-5de79ce6490141caa6596b0794b5bcf4
Source dataset
uspto-grants-2015_12
Patent number
US09212154B2

Reaction notes

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