Acetic Anhydride → HCID 178477172, compound

HRID 2077107Notes

Reaction equation

HRID 2077107 reaction equation
[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11](=[O:23])[C:12]([CH3:22])([S:14][CH2:15][CH:16]2[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]2)[CH3:13])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.[C:33](OC(=O)C)(=[O:35])[CH3:34]>>[C:33]([SH:14]([CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]1)[C:12]([CH3:13])([CH3:22])[C:11]([NH:10][C:7]1[CH:6]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[O:9][N:8]=1)=[O:23])(=[O:35])[CH3:34]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 59704015N-(5-tert-butyl-isoxazol-3-yl)-2-methyl-2-(piperidin-3-ylmethylsulfanyl)-propionamide

Product 1

HCID 178477172HCID 178477172, compound

Procedure

A solution of 175 mg (0.52 mmol) of N-(5-tert-butyl-isoxazol-3-yl)-2-methyl-2-(piperidin-3-ylmethylsulfanyl)-propionamide 0.18 mL (1.04 mmol) of N,N-diisopropylethylamine and acetic anhydride (1.5 mL) were heated for 0.5 h to 100° C. within a microwave (CEM discover). The solvent was removed under reduced pressure. The residue was dissolved in DCM (5 mL) and washed with saturated aqueous NaHCO3 solution (5 mL). The organic phase was dried over Na2SO4, filtered and the filtrate concentrated under reduced pressure to afford 183 mg of 2-(1-acetyl-piperidin-3-ylmethylsulfanyl)-N-(5-tert-butyl-isoxazol-3-yl)-2-methyl-propionamide, which was used in the next step without further purification.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in DCM (5 mL)
  3. washwashed with saturated aqueous NaHCO3 solution (5 mL)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-075950424ec6453c979adf05b2907575
Source dataset
uspto-grants-2011_04
Patent number
US07928123B2

Reaction notes

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