Acetic Anhydride → HCID 90203919, compound

HRID 1480179Notes

Reaction equation

HRID 1480179 reaction equation
[CH2:1]([O:8][CH2:9][C:10]([NH:16][S:17]([C:19]([CH3:22])([CH3:21])[CH3:20])=[O:18])([CH3:15])/[C:11](=[N:13]/[OH:14])/[NH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:29](OC(=O)C)(=O)[CH3:30]>CN(C=O)C>[CH2:1]([O:8][CH2:9][C:10]([NH:16][S:17]([C:19]([CH3:22])([CH3:21])[CH3:20])=[O:18])([CH3:15])[C:11]1[N:12]=[C:29]([CH3:30])[O:14][N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 90203553HCID 90203553, compound

Product 1

HCID 90203919HCID 90203919, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (Z)-3-(benzyloxy)-2-(1,1-dimethylethylsulfinamido)-N′-hydroxy-2-methylpropanimidamide (Example 112b, 1.25 g, 3.82 mmol) in dry DMF (25 ml) was added potassium carbonate (633 mg, 4.58 mmol) followed by addition of acetic anhydride (390 mg, 360 uL, 3.82 mmol). The reaction mixture was stirred at room temperature for 1 hour and was then stirred at 120° C. for 2 hours. DMF was removed in vacuo and the residue was dissolved in ethyl acetate which was extracted with a 1.0M aqueous solution of sodium bicarbonate. The organic phase was dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a heptane/ethylacetate gradient to yield the title compound (1.20 g, purity: 80%, 72%) as a light yellow oil. MS (ESI, m/z): 352.6 (M+H+).

Workup

  1. stirringwas then stirred at 120° C. for 2 hours
  2. customDMF was removed in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate which
  4. extractionwas extracted with a 1.0M aqueous solution of sodium bicarbonate
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. customevaporated down to dryness
  7. customThe crude material was purified by flash chromatography on silica eluting with a heptane/ethylacetate gradient

Sources & evidence

ORD record
ord-6f1562aca7644b3f8fe0858f42678f8e
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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