Acetic Acid → HCID 68706406, compound

HRID 2201961Notes

Reaction equation

HRID 2201961 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[C-:5]#N.[Na+].[C:8]([Si:12]([CH3:42])([CH3:41])[O:13][C@H:14]([C:20]1[CH:25]=[CH:24][C:23]([C:26]2[C@@H:27]([CH2:31][CH2:32][CH2:33][C:34]3[S:38]C(C=O)=[CH:36][CH:35]=3)[CH2:28][CH2:29][CH:30]=2)=[CH:22][CH:21]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])([CH3:11])([CH3:10])[CH3:9]>CO.O=[Mn]=O>[CH3:5][O:3][C:1]([C:2]1[S:38][C:34]([CH2:33][CH2:32][CH2:31][C@H:27]2[CH2:28][CH2:29][CH:30]=[C:26]2[C:23]2[CH:22]=[CH:21][C:20]([C@@H:14]([O:13][Si:12]([C:8]([CH3:10])([CH3:9])[CH3:11])([CH3:41])[CH3:42])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:25][CH:24]=2)=[CH:35][CH:36]=1)=[O:4]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8929Sodium CyanideHCID 86642144HCID 86642144, compound

Product 1

HCID 68706406HCID 68706406, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 887MethanolSolvent

Procedure

Acetic acid (12 μL, 0.21 mmol), NaCN (25 mg, 0.51 mmol) and MnO2 (152 mg, 1.7 mmol) were added to a mixture of 42a (43 mg, 0.084 mmol) in methanol (0.5 mL). The mixture was stirred for 18 h and then was filtered through Celite, washing with ethyl acetate. The filtrate was washed with water (20 mL) and the aqueous layer was further extracted with ethyl acetate (20 mL). The combined ethyl acetate solution was dried (Na2SO4), filtered and evaporated to give the title compound (45 mg, 0.083 mmol, 99%).

Workup

  1. filtrationwas filtered through Celite
  2. washwashing with ethyl acetate
  3. washThe filtrate was washed with water (20 mL)
  4. extractionthe aqueous layer was further extracted with ethyl acetate (20 mL)
  5. dry with materialThe combined ethyl acetate solution was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-080b7793ea8b482eb93f88056bfeb627
Source dataset
uspto-grants-2016_06
Patent number
US09365485B2

Reaction notes

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