Triethylamine → BIS THF HNS Derivative 2

HRID 598806Notes

Reaction equation

HRID 598806 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.[CH2:19](N(CC)CC)[CH3:20].[CH3:26][CH2:27][O:28][C:29]([CH3:31])=[O:30]>C(#N)C>[O:28]1[C@H:29]2[O:30][CH2:19][CH2:20][C@H:31]2[C@H:26]([O:8][C:9](=[O:10])[O:11][N:12]2[C:13](=[O:14])[CH2:15][CH2:16][C:17]2=[O:18])[CH2:27]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 676246Di(succinimido) carbonate

Product 1

HCID 11391603BIS THF HNS Derivative 2

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 13 (2 g, 15.3 mmol), N,N′-disuccinimidyl carbonate (4.76 g, 18.5 mmol), and triethylamine (Et3N) (4.12 g, 40.8 mmol) in acetonitrile (CH3CN) (50 mL) were stirred for 24 hours. The reaction mixture then was diluted with EtOAc (100 ml), washed several times with brine, then dried over anhydrous Na2SO4 and concentrated under reduced pressure to provide crude compound 15, which was purified by column chromatography to obtain the active carbonate 15. Yield (3.1 g, 75%), m.p 128-130° C. 1H NMR (CDCl3, 200 MHz): δ 5.74 (d, 1H, J=5.1 Hz), 5.26 (m, 1H), 4 (m, 4H), 3.1 (m, 1H), 2.84 (s, 4H), 1.88-2.2 (m, 2H).

Workup

  1. washwashed several times with brine
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customto provide crude compound 15, which
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-5a654a1b53484783b77c9e905b387f49
Source dataset
uspto-grants-2011_03
Patent number
US07897635B2

Reaction notes

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