HCID 12069904, compound → HCID 69810410, compound

HRID 1805408Notes

Reaction equation

HRID 1805408 reaction equation
[N+:1]([C:4]1[CH:38]=[CH:37][C:7]([CH2:8][CH:9]([CH2:19][N:20]([CH2:33][C:34]([OH:36])=[O:35])[CH2:21][CH2:22][CH2:23][N:24]([CH2:29][C:30]([OH:32])=[O:31])[CH2:25][C:26]([OH:28])=[O:27])[N:10]([CH2:15][C:16]([OH:18])=[O:17])[CH2:11][C:12]([OH:14])=[O:13])=[CH:6][CH:5]=1)([O-])=O>[Pd].CC#N>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][CH:9]([CH2:19][N:20]([CH2:33][C:34]([OH:36])=[O:35])[CH2:21][CH2:22][CH2:23][N:24]([CH2:25][C:26]([OH:28])=[O:27])[CH2:29][C:30]([OH:32])=[O:31])[N:10]([CH2:15][C:16]([OH:18])=[O:17])[CH2:11][C:12]([OH:14])=[O:13])=[CH:37][CH:38]=1

Participants

4

Reactant 1

HCID 12069904HCID 12069904, compound

Product 1

HCID 69810410HCID 69810410, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6342AcetonitrileSolvent

Procedure

1.03 g (1.25 mmol) of NO2-Bz-TTDA was dissolved into 50 mL of CH3CN, and was mixed with 24.8 mg of Pd/C to form a reaction solution. The reaction solution was charged into a reactor. The reactor was vacuumed for 3 minutes, followed by introducing H2 therein to adjust the pressure to 1.5 kg/cm2, allowing reaction to take place by stirring at room temperature for 4 hours, and evaporating when the pressure in the reactor was kept constant to form a crude product. The crude product was purified using silica column chromatography (eluent: CH2Cl2/CH3OH=19/1) so as to obtain a product of 0.82 g (1.03 mmol, 82.4%) of NH2-Bz-TTDA.

Workup

  1. customto form a reaction solution
  2. additionThe reaction solution was charged into a reactor
  3. additionby introducing H2
  4. customreaction
  5. customevaporating when the pressure in the reactor
  6. customto form a crude product
  7. customThe crude product was purified

Sources & evidence

ORD record
ord-4278942b83ca45f98470b6d1c22a5ccd
Source dataset
uspto-grants-2013_01
Patent number
US08354512B2

Reaction notes

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