Acetic Acid → HCID 58636780, compound

HRID 1158980Notes

Reaction equation

HRID 1158980 reaction equation
[C:1]([O:5][C:6](=[O:36])[N:7]([CH2:16][C:17]1[CH:18]=[N:19]C(C=O)=[C:21]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]#[N:33])[CH:27]=2)[C:22]=1[CH3:23])[C:8]1[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[C-:37]#N.[Na+].[C:40]([OH:43])(=[O:42])[CH3:41]>CO.[O-2].[O-2].[Mn+4]>[CH3:37][O:42][C:40]([C:41]1[C:21]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]#[N:33])[CH:27]=2)=[C:22]([CH3:23])[C:17]([CH2:16][N:7]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:36])[C:8]2[CH:9]=[CH:10][C:11]([C:14]#[N:15])=[CH:12][CH:13]=2)=[CH:18][N:19]=1)=[O:43]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8929Sodium CyanideHCID 58636757HCID 58636757, compound

Product 1

HCID 58636780HCID 58636780, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of [5-(3-cyano-benzyloxy)-6-formyl-4-methyl-pyridin-3-ylmethyl]-(4-cyano-phenyl)-carbamic acid tert-butyl ester (141) (140 mg, 0.3 mmol), sodium cyanide (272 mg, 5.5 mmol), manganese (IV) dioxide (422 mg, 85%, 0.29 mmol), acetic acid (256 mg, 4.2 mmol) in methyl alcohol (40 mL) was stirred at room temperature for 12 hours. The solid was filtered through a celite pad and washed several times with methanol. The filtrate was evaporated to give a crude residue, which was purified by column chromatography on silica gel using a gradient mixture of ethyl acetate:hexane (0:1 to 1:0) as eluant to give 5-{[tert-butoxycarbonyl-(4-cyano-phenyl)-amino]-methyl}-3-(3-cyano-benzyloxy)-4-methyl-pyridine-2-carboxylic acid methyl ester (143) (142 mg, 96% yield) as a light yellow oil.

Workup

  1. filtrationThe solid was filtered through a celite pad
  2. washwashed several times with methanol
  3. customThe filtrate was evaporated
  4. customto give a crude residue, which
  5. customwas purified by column chromatography on silica gel using
  6. additiona gradient mixture of ethyl acetate:hexane (0:1 to 1:0) as eluant

Sources & evidence

ORD record
ord-8201b6aac06d4f8b8cc6dfff6f0eee42
Source dataset
uspto-grants-2010_10
Patent number
US07812037B2

Reaction notes

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