Triethylamine → HCID 42625373, compound

HRID 1174198Notes

Reaction equation

HRID 1174198 reaction equation
[C:1]([O:5][C:6]([C@H:8]([NH:13][CH2:14][CH2:15][NH:16][CH2:17][C:18]1[N:23]=[C:22]([C:24]([O:26][CH3:27])=[O:25])[CH:21]=[CH:20][CH:19]=1)[C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:28](=O)(ON1C(=O)CCC1=O)[O:29]N1C(=O)CCC1=O.C(N(CC)CC)C>ClCCCl.ClC(Cl)C>[C:1]([O:5][C:6]([C@@H:8]([N:13]1[CH2:14][CH2:15][N:16]([CH2:17][C:18]2[N:23]=[C:22]([C:24]([O:26][CH3:27])=[O:25])[CH:21]=[CH:20][CH:19]=2)[C:28]1=[O:29])[C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 676246Di(succinimido) carbonateHCID 67406583HCID 67406583, compound

Product 1

HCID 42625373HCID 42625373, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

A solution of the product of Example 50-3 (92 g, 243 mmol), disuccinimidyl carbonate (78 g, 304 mmol), and triethylamine (41 mL, 294 mmol) in 1,2-dichloroethane (1.8 L) was stirred at room temperature for 16 hours. The mixture was diluted with dichloroethane (200 mL), washed with saturated NaHCO3 (2×500 mL), and brine (200 mL), dried over MgSO4, filtered and concentrated. The residue was triturated with hexane (550 mL) and ethyl acetate (50 mL) at room temperature for two hours to give the title compound as a white solid (85 gm, 98% yield). 1H NMR (CDCl3): δ ppm 1.10 (s, 9 H), 1.48 (s, 9 H), 3.34 (m, 2 H), 3.62 (m, 1 H), 3.88 (m, 1 H), 4.00 (s, 3 H), 4.42 (s, 1 H), 4.64 (s, 2 H), 7.52 (d, 1 H), 7.81 (t, 1 H), 8.03 (d, 1 H).

Workup

  1. washwashed with saturated NaHCO3 (2×500 mL), and brine (200 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was triturated with hexane (550 mL) and ethyl acetate (50 mL) at room temperature for two hours

Sources & evidence

ORD record
ord-be8eda9792a5422db68bd348accbf286
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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