Acetonitrile--water (1/1) → HCID 11110226, compound

HRID 376783Notes

Reaction equation

HRID 376783 reaction equation
[C:1]([O:4][CH:5]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][C:27](=[O:29])[NH2:28])[CH:20]=1)[CH:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)C1SCCCS1)(=[O:3])[CH3:2].C(#N)C.[OH2:33]>>[C:1]([O:4][CH:5]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][C:27](=[O:29])[NH2:28])[CH:20]=1)[C:6](=[O:33])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 18373917Acetonitrile--water (1/1)HCID 53730221HCID 53730221, compound

Product 1

HCID 11110226HCID 11110226, compound

Procedure

To a solution of (±)-1-acetoxy-1-(3-carbamylmethoxyphenyl)-2-phenyl-2-(1,3-dithian-2-yl)-ethane (110 mg, 0.26 mmol) in 5 mL 9:1 (v/v) acetonitrile/water was added mercuric perchiorate (148 mg, 0.33 mmol). The solution was stirred for 15 min, filtered through a 0.45 mm PTFE syringe filter (Gelman) into a 5% sodium bicarbonate solution (10 mL), and extracted with 50 mL dichloromethane. The organic phase was dried and evaporated under reduced pressure to yield a colorless oil. Samples for analysis were evaporated from methanol, dissolved in warm water and lyophilized. Yield: 65 mg (76%). IR: 3445, 1743, 1694, 1462, 1236, 1075, 720 cm-1. 1H NMR (CDCl3, TMS) d 7.936 (d, J=7.82 Hz, 2 H), 7.529 (t, J=7.56 Hz, 1 H), 7.412 (t, J=7.57 Hz, 2 H), 7.319 (t, J=7.86 Hz, 1 H), 7.139 (d, J=7.51 Hz, 1 H), 7.051 (s, 1 H), 6.884 (dd, J=8.21, 2.75 Hz, 1 H) 6.835 (s, 1 H), 6.558 (s, 1 H), 6.148 (s, 1 H), 4.462 (s, 2 H), 2.207 (s, 3 H). 13C NMR (CDCl3, TMS) d 193.577, 170.825, 170.348, 157.593, 135.473, 134.494, 133.637, 130.516, 128.768, 128.711, 122.371, 115.205, 115.140, 77.144, 67.115, 20.715. Anal. Calcd. for C18H17NO5.H2O: C, 62.59; H, 5.54; N, 4.05. Found: C, 62.53; H, 5.12; N, 3.90.

Workup

  1. filtrationfiltered through a 0.45 mm PTFE syringe
  2. filtrationfilter (Gelman) into a 5% sodium bicarbonate solution (10 mL)
  3. extractionextracted with 50 mL dichloromethane
  4. customThe organic phase was dried
  5. customevaporated under reduced pressure
  6. customto yield a colorless oil
  7. customSamples for analysis were evaporated from methanol
  8. dissolutiondissolved in warm water

Sources & evidence

ORD record
ord-897f38866fea43bda1c77cf7e5abd8e0
Source dataset
uspto-grants-2000_02
Patent number
US06022529

Reaction notes

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