Ninhydrin → HCID 12803412, compound

HRID 2285795Notes

Reaction equation

HRID 2285795 reaction equation
[CH2:1]1[S:18][CH:5]([CH2:6][C@@H:7]([N:15]=[N+]=[N-])[C@H:8]([C:12]([OH:14])=[O:13])[C@@H:9]([CH3:11])[OH:10])[S:4][CH2:3][CH2:2]1.C1C=C2C(C(O)(O)C(=O)C2=CC=1)=O>CO.[Pd]>[CH2:3]1[S:4][CH:5]([CH2:6][C@@H:7]([NH2:15])[C@H:8]([C:12]([OH:14])=[O:13])[C@@H:9]([CH3:11])[OH:10])[S:18][CH2:1][CH2:2]1

Participants

5

Reactant 2

HCID 10236NinhydrinHCID 12803410HCID 12803410, compound

Product 1

HCID 12803412HCID 12803412, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-azido-4-C-carboxy-2,3,4,6-tetradeoxy-D-arabino-hexose trimethylene dithioacetal (920 mg, 3.01 mmol) and 5% palladium-on-charcoal (375 mg) in methanol (25 ml) is hydrogenated at a pressure of 1 atmosphere for 5 hours at room temperature. The catalyst is then removed by filtration through Celite and the filtrate evaporated and dried in vacuo to give TLC-chromatographically-homogeneous, ninhydrin-positive amino acid trimethylene dithioacetal; yield 816 mg (97%).

Workup

  1. customThe catalyst is then removed by filtration through Celite
  2. customthe filtrate evaporated
  3. customdried in vacuo
  4. customto give TLC-chromatographically-homogeneous

Sources & evidence

ORD record
ord-0182a55c6e664358bfc90b3182d51a14
Source dataset
uspto-grants-1982_04
Patent number
US04324900

Reaction notes

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