Triethylamine → BIS THF HNS Derivative 2

HRID 1372184Notes

Reaction equation

HRID 1372184 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-bd525df44b5b4f50a7e44aad7532f168
Source dataset
uspto-grants-2007_01
Patent number
US07157489B2

Reaction notes

Loading…