Acetonitrile → Carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester 2-(2-hexadecyl-2,5,7,8-tetramethyl-chroman-6-yloxy)-ethyl Ester

HRID 2402996

Reaction equation

HRID 2402996 reaction equation
[CH2:1]([C:17]1([CH3:34])[CH2:26][CH2:25][C:24]2[C:19](=[C:20]([CH3:33])[C:21]([CH3:32])=[C:22]([O:28][CH2:29][CH2:30][OH:31])[C:23]=2[CH3:27])[O:18]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[C:35](=O)([O:44]N1C(=O)CCC1=O)[O:36][N:37]1[C:41](=[O:42])[CH2:40][CH2:39][C:38]1=[O:43].C(N(CC)CC)C.C(#N)C>ClCCl>[CH2:1]([C:17]1([CH3:34])[CH2:26][CH2:25][C:24]2[C:19](=[C:20]([CH3:33])[C:21]([CH3:32])=[C:22]([O:28][CH2:29][CH2:30][O:31][C:35](=[O:44])[O:36][N:37]3[C:41](=[O:42])[CH2:40][CH2:39][C:38]3=[O:43])[C:23]=2[CH3:27])[O:18]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 676246Di(succinimido) carbonateHCID 593472622-(2-Hexadecyl-2,5,7,8-tetramethyl-chroman-6-yloxy)-ethanol

Product 1

HCID 59347260Carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester 2-(2-hexadecyl-2,5,7,8-tetramethyl-chroman-6-yloxy)-ethyl EsterYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 17 (10.5 g, 22 mmol) was dissolved in anhydrous dichloromethane (150 mL). To the solution were added disuccinimidyl carbonate (8.45 g, 33 mmol), triethylamine (20 mL) and acetonitrile (50 mL). The reaction mixture was stirred at room temperature under argon for over night and then evaporated dryness. The residue was dissolved in dichloromethane (300 mL). It was washed with saturated NaHCO3 aqueous solution (3×100 mL). The organic layer was dried over Na2SO4, filtered and evaporated to dryness. Compound 18 (10.4 g, 77%) was obtained as colorless powder after drying in high vacuum, which was directly used for the next step without further purification.

Workup

  1. customevaporated dryness
  2. dissolutionThe residue was dissolved in dichloromethane (300 mL)
  3. washIt was washed with saturated NaHCO3 aqueous solution (3×100 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-b93fad99f53043dba0a407b85a80e063
Source dataset
uspto-grants-2014_08
Patent number
US08796436B2

Linked notes

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