Acetonitrile → HCID 58779147, compound

HRID 598809Notes

Reaction equation

HRID 598809 reaction equation
C1C(=O)N([O:8][C:9]([O:11][N:12]2[C:17](=[O:18])[CH2:16][CH2:15][C:13]2=[O:14])=[O:10])C(=O)C1.CC[N:21]([CH2:24][CH3:25])[CH2:22][CH3:23].[CH3:26][C:27]#N>>[N:21]1[C:22]2[C:23](=[CH:13][CH:15]=[CH:16][CH:17]=2)[C:26]([CH2:27][O:8][C:9](=[O:10])[O:11][N:12]2[C:13](=[O:14])[CH2:15][CH2:16][C:17]2=[O:18])=[CH:25][CH:24]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 676246Di(succinimido) carbonate

Product 1

HCID 58779147HCID 58779147, compoundYield 58%

Procedure

The alcohol (50 mg, 0.31 mmol), N,N′-disuccinimidyl carbonate (1128 mg, 0.5 mmol), and Et3N (63 mg, 0.63 mmol) in CH3CN (2 mL) were stirred for 12 hours. After dilution with EtOAc (10 mL) and washing several times with brine (3×10 mL), the organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel chromatography to obtain compound 31 (52 mg, 58%) as solid. M.P.: 94° C. 1H NMR (CDCl3, 400 MHz): δ 8.9 (d, 1H, J=4.4 Hz), 8.1 (d, 1H, J=8.5 Hz), 7.9 (d, 1H, J=8.3 Hz), 7.74 (m, 1H) 7.63 (m, 1H), 7.49 (d, 1H, J=4.3 Hz), 2.84 (s, 4H).

Workup

  1. washAfter dilution with EtOAc (10 mL) and washing several times with brine (3×10 mL)
  2. dry with materialthe organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-b0109fc70613428da31eb8f5e093c6f0
Source dataset
uspto-grants-2011_03
Patent number
US07897635B2

Reaction notes

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