Acetic Acid → HCID 15887793, compound

HRID 381487Notes

Reaction equation

HRID 381487 reaction equation
[C:1]1([CH:7]2[C:19]3[NH:18][C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:11]=3[CH2:10][CH2:9][N:8]2[C:20](=[O:31])/[CH:21]=[CH:22]/[C:23]2[CH:28]=[CH:27][C:26]([CH:29]=[O:30])=[CH:25][CH:24]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C-]#N.[Na+].[C:35](O)(=[O:37])C>CO.O=[Mn]=O>[O:31]=[C:20]([N:8]1[CH2:9][CH2:10][C:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:18][C:19]=2[CH:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)/[CH:21]=[CH:22]/[C:23]1[CH:28]=[CH:27][C:26]([C:29]([O:37][CH3:35])=[O:30])=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8929Sodium CyanideHCID 9931174HCID 9931174, compound

Product 1

HCID 15887793HCID 15887793, compoundYield 70.1%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of Example 9 (0.2 g, 0.49 mmol) in 20 mL of MeOH was added activated MnO2 (0.59 g, 14 equiv.), sodium cyanide (0.05 g, 2 equiv.) and acetic acid (0.05 g, 1.7 equiv.). The resulting mixture was stirred for 5 hours. Tlc monitoring showed a new compound (SiO2,DCM:MeOH (95:5), Rf=0.82). The mixture was filtered through a short column of celite using 150 mL of a mixture of MeOH:EtOAc:CHCl3 (1:25:25). After evaporation in vacuo the residue was purified via flash chromatography on a 2×20 cm2 column using DCM as eluting solvent. Evaporation and recrystallization from EtOH gave the title compound (0.15 g, 70%) as yellow crystals.

Workup

  1. filtrationThe mixture was filtered through a short column
  2. customAfter evaporation in vacuo the residue
  3. customwas purified via flash chromatography on a 2×20 cm2 column
  4. washas eluting solvent
  5. customEvaporation and recrystallization from EtOH

Sources & evidence

ORD record
ord-f393763fd609403299c617bd255b3f71
Source dataset
uspto-grants-2001_10
Patent number
US06306870B1

Reaction notes

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