Diisopropylethylamine → HCID 58079444, compound

HRID 444991Notes

Reaction equation

HRID 444991 reaction equation
[C:1]([O:5][C:6](=[O:38])[C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:10]([OH:12])=[O:11])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[B-](F)(F)(F)F.CN(C(O[N:61]1[C:66](=[O:67])[CH2:65][CH2:64][C:62]1=[O:63])=[N+](C)C)C>C1COCC1>[O:63]=[C:62]1[CH2:64][CH2:65][C:66](=[O:67])[N:61]1[O:11][C:10](=[O:12])[C:9]1[CH:13]=[CH:14][C:15]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[C:7]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:38])[CH:8]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 58079467HCID 58079467, compound

Product 1

HCID 58079444HCID 58079444, compoundYield 101.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-(14-tert-Butoxycarbonyl tetradecyloxy) isophthalic acid 3-tert-butyl ester (0.15 g, 0.28 mmol) was dissolved in THF (2 ml). DIEA (58 μl, 0.34 mmol) was added, and the solution was cooled to 0° C. TSTU (0.10 g, 0.28 mmol) was added. The reaction was stirred at 0° C. for 30 min and then at rt for 16 h. The sample was concentrated under vacuum to near dryness. AcOEt (20 ml) was added and the solution was washed with 0.2 N HCl and sat. NaHCO3 (3×5 ml each), dried over MgSO4 and concentrated to yield a residue (0.18 g). The residue was purified by flash chromatography (silica: AcOEt/heptane 3:7 (0.5 l), 1:1 (0.2 l)) yielding an oil with white solids (55 mg, 31%).

Workup

  1. waitat rt for 16 h
  2. concentrationThe sample was concentrated under vacuum
  3. additionAcOEt (20 ml) was added
  4. washthe solution was washed with 0.2 N HCl and sat. NaHCO3 (3×5 ml each)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-45057b1330184e82a21ee4f810741584
Source dataset
uspto-grants-2013_07
Patent number
US08476228B2

Reaction notes

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