Formic Acid → HCID 21070329, compound

HRID 1371542Notes

Reaction equation

HRID 1371542 reaction equation
[C:1]([C:3]1[CH:42]=[CH:41][C:6]([CH2:7][CH:8]([NH:16][C:17](=[O:40])[CH2:18][CH:19]([NH:26][S:27]([C:30]2[CH:39]=[CH:38][C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:31]=2)(=[O:29])=[O:28])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:9](=[O:15])[N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:5][CH:4]=1)#N.C(O)=[O:44]>[Al].[Ni]>[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][CH:8]([NH:16][C:17](=[O:40])[CH2:18][CH:19]([NH:26][S:27]([C:30]2[CH:39]=[CH:38][C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:31]=2)(=[O:28])=[O:29])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:9](=[O:15])[N:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)=[CH:41][CH:42]=1)=[O:44]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 21070315HCID 21070315, compound

Product 1

HCID 21070329HCID 21070329, compound

Reagents, catalysts & solvents 1

HCID 6336846Nickel aluminideCatalyst

Procedure

3 g of aluminium/nickel alloy are added to a mixture of 3 g of the compound obtained in step A of Example 1 and 40 ml of 75% formic acid, and the mixture is refluxed for 2 hours. The insoluble material is filtered off by suction while hot and washed with MeOH, and the filtrate is concentrated under vacuum. The residue is taken up in chloroform, the insoluble material is filtered off by suction and washed with an MeOH/chloroform mixture, and the filtrate is concentrated under vacuum. The residue is taken up in chloroform and filtered, the filtrate is washed with saturated NaHCO3 solution and with saturated NaCl solution and dried over Na2SO4, and the solvent is evaporated off under vacuum. 2.4 g of the expected product are obtained.

Workup

  1. temperaturethe mixture is refluxed for 2 hours
  2. filtrationThe insoluble material is filtered off by suction while hot and
  3. washwashed with MeOH
  4. concentrationthe filtrate is concentrated under vacuum
  5. filtrationthe insoluble material is filtered off by suction
  6. washwashed with an MeOH/chloroform mixture
  7. concentrationthe filtrate is concentrated under vacuum
  8. filtrationfiltered
  9. washthe filtrate is washed with saturated NaHCO3 solution and with saturated NaCl solution
  10. dry with materialdried over Na2SO4
  11. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-3c272b436c8b456c92e14fbee2d3ceca
Source dataset
uspto-grants-2007_01
Patent number
US07157454B2

Reaction notes

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