Ninhydrin → HCID 13365732, compound

HRID 2412348Notes

Reaction equation

HRID 2412348 reaction equation
[N:1]([C@H:4]1[C@H:11]([C:12]([O:14][CH3:15])=[O:13])[C@@H:10]([CH3:16])[O:9][C@H:6]([O:7][CH3:8])[CH2:5]1)=[N+]=[N-].C1C=C2C(C(O)(O)C(=O)C2=CC=1)=O>CO.[Pd]>[NH2:1][C@H:4]1[C@H:11]([C:12]([O:14][CH3:15])=[O:13])[C@@H:10]([CH3:16])[O:9][C@H:6]([O:7][CH3:8])[CH2:5]1

Participants

5

Reactant 2

HCID 10236NinhydrinHCID 13365730HCID 13365730, compound

Product 1

HCID 13365732HCID 13365732, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl 3-azido-4-C-carbomethoxy-2,3,4,6-tetradeoxy-α-D-arabino-hexopyranoside (1.19 g, 5.19 mmol) and 5% palladium-on-charcoal (500 mg) in methanol (35 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 ester; yield 1.01 g (96%).

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-66ac63fb64b64f69bf95b7f503702646
Source dataset
uspto-grants-1985_01
Patent number
US04491659

Reaction notes

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