Triethylamine → HCID 67406816, compound

HRID 1174358Notes

Reaction equation

HRID 1174358 reaction equation
[OH:1][C:2]1[CH:24]=[CH:23][CH:22]=[CH:21][C:3]=1[CH2:4][NH:5][CH2:6][CH2:7][NH:8][C@H:9]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:10]([CH3:13])([CH3:12])[CH3:11].[C:25](=O)(ON1C(=O)CCC1=O)[O:26]N1C(=O)CCC1=O.C(N(CC)CC)C>ClC(Cl)C>[OH:1][C:2]1[CH:24]=[CH:23][CH:22]=[CH:21][C:3]=1[CH2:4][N:5]1[CH2:6][CH2:7][N:8]([C@@H:9]([C:10]([CH3:13])([CH3:12])[CH3:11])[C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])[C:25]1=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 676246Di(succinimido) carbonateHCID 67406605HCID 67406605, compound

Product 1

HCID 67406816HCID 67406816, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of Example 145A (180 mg, 0.521 mmol) and disuccinimidyl carbonate (0.16 g, 0.625 mmol) in dichloroethane (5 mL) was treated with triethylamine (87 μL, 0.625 mmol) at 25° C. for 16 h. The mixture was partitioned between 10% sodium carbonate and dichloromethane. The organic layer was separated, washed with brine, dried over MgSO4, filtered, and the solvents were evaporated to give the crude residue which was purified using silica gel chromatography eluting with a gradient of 100% hexanes to 60% hexanes in ethyl acetate to give the title compound (0.127 g, 67%).

Workup

  1. customThe mixture was partitioned between 10% sodium carbonate and dichloromethane
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were evaporated
  7. customto give the crude residue which
  8. customwas purified
  9. washeluting with a gradient of 100% hexanes to 60% hexanes in ethyl acetate

Sources & evidence

ORD record
ord-052a89a3eb2e46d88101b4ccbe0acbac
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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