Acetic Anhydride → HCID 10215483, compound

HRID 1823334Notes

Reaction equation

HRID 1823334 reaction equation
[CH3:1][O:2][C@H:3]([CH3:22])[C@H:4]([NH:20][OH:21])[CH2:5][S:6]([CH2:9][C:10]1[CH:11]=[N:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:8])=[O:7].[C:23](OC(=O)C)(=[O:25])C>C(O)=O>[CH3:1][O:2][C@H:3]([CH3:22])[C@H:4]([N:20]([OH:21])[CH:23]=[O:25])[CH2:5][S:6]([CH2:9][C:10]1[CH:11]=[N:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:7])=[O:8]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 58630860HCID 58630860, compound

Product 1

HCID 10215483HCID 10215483, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

(2S,3R)-N-[3-Methoxy-1-(3-quinolylmethanesulfonyl)-2-butyl]hydroxylamine (300 mg) was dissolved in a premixed solution of acetic anhydride (2 ml) and formic acid (6 ml) and stood overnight. The reaction was evaporated and then re-evaporated from chloroform (2×5 ml). The residue was redissolved in methanol (5 ml), treated with potassium carbonate (639 mg) and stirred for 45 min and then evaporated. The residue was redissolved in water (5 ml) and the pH adjusted to 7 with 1M hydrochloric acid. After extraction with MDC (2×5 ml), the combined extracts were dried (MgSO4) and evaporated. The residue was chromatographed (acid washed silica gel, 3% MeOH/MDC) to give the title compound (232 mg). MS (APCI+ve ion) 353 (MH+); 1H NMR δ[(CD3)2SO] 9.9 and 9.7 (1H, 2xs rotamers), 8.83 (1H, m), 8.38 (1H,d,J=2 Hz), 8.32 and 8.0 (1H,2xs rotamers), 8.03 (2H, m), 7.81 (1H, t, J=8 Hz), 7.66 (1H, t, J=8 Hz), 4.85 and 4.22(1H, 2xs rotamers), 4.76 (2H, m), 3.7–3.3 (3H, m), 3.25 (3H, s), 1.15 (3H, m rotamers).

Workup

  1. customThe reaction was evaporated
  2. customre-evaporated from chloroform (2×5 ml)
  3. dissolutionThe residue was redissolved in methanol (5 ml)
  4. additiontreated with potassium carbonate (639 mg)
  5. customevaporated
  6. dissolutionThe residue was redissolved in water (5 ml)
  7. extractionAfter extraction with MDC (2×5 ml)
  8. dry with materialthe combined extracts were dried (MgSO4)
  9. customevaporated
  10. customThe residue was chromatographed
  11. wash(acid washed silica gel, 3% MeOH/MDC)

Sources & evidence

ORD record
ord-97ef39c13a6e4e349f03bfb1237eb7e9
Source dataset
uspto-grants-2006_05
Patent number
US07038055B2

Reaction notes

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