Acetic Anhydride → HCID 11712603, compound

HRID 1008770Notes

Reaction equation

HRID 1008770 reaction equation
[C:1](OC(=O)C)(=[O:3])C.[O:8]1[C:12]2[CH:13]=[CH:14][C:15]([C:17]#[C:18][CH:19]([NH:37][OH:38])[CH2:20][S:21]([N:24]3[CH2:29][CH2:28][N:27]([C:30]4[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=4)[CH2:26][CH2:25]3)(=[O:23])=[O:22])=[CH:16][C:11]=2[O:10][CH2:9]1>C1COCC1.C(O)=O>[O:8]1[C:12]2[CH:13]=[CH:14][C:15]([C:17]#[C:18][CH:19]([N:37]([OH:38])[CH:1]=[O:3])[CH2:20][S:21]([N:24]3[CH2:25][CH2:26][N:27]([C:30]4[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=4)[CH2:28][CH2:29]3)(=[O:23])=[O:22])=[CH:16][C:11]=2[O:10][CH2:9]1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 11517978HCID 11517978, compound

Product 1

HCID 11712603HCID 11712603, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Acetic anhydride (1.00 mL; 10.59 mmol) was added dropwise to formic acid (5 mL) at 0° C. and the mixture was stirred for 30 min. 1 mL of this solution was then added to a solution of N-[3-(1,3-benzodioxol-5-yl)-1-({[4-(4-fluorophenyl)-1-piperazinyl]sulfonyl}methyl)-2-propynyl]hydroxylamine (150.0 mg; 0.34 mmol) in THF (3 mL) and formic acid (0.7 mL) and the mixture was stirred overnight. The reaction mixture was then evaporated to dryness, the residue dissolved in MeOH and heated at 60° C. for 3 h. The solution was allowed to cool down to rt and the precipitate obtained was filtered. It was redissolved in EtOAc and precipitated again in pentane, filtered and dried under reduced pressure to give the title compound (1) (80 mg, 50% yield) as a white solid. HPLC, Rt: 3.58 min (purity: 96.9%). LC/MS, M+(ESI): 476.3, M−(ESI): 474.3. 1H NMR (CDCl3) δ: 9.55 (s, 0.5H), 9.12 (s, 0.5H), 8.1 (m, 1H), 6.90-7.09 (m, 7H), 6.05 (s, 2H), 4.81 (s, 0.5H), 4.61 (s, 0.5H), 3.62 (m, 2H), 3.31 (m, 4H), 3.14 (m, 4H).

Workup

  1. stirringthe mixture was stirred overnight
  2. customThe reaction mixture was then evaporated to dryness
  3. dissolutionthe residue dissolved in MeOH
  4. temperatureto cool down to rt
  5. customthe precipitate obtained
  6. filtrationwas filtered
  7. dissolutionIt was redissolved in EtOAc
  8. customprecipitated again in pentane
  9. filtrationfiltered
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-fe06f70ef28b4fbfb31176ef2a7fa540
Source dataset
uspto-grants-2011_07
Patent number
US07973039B2

Reaction notes

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