Diisopropylethylamine → 5-{9-[3-(2,5-Dioxo-pyrrolidin-1-yloxycarbonyl)-propylcarbamoyl]-nonyloxy}-isophthalic acid di-tert-butyl ester

HRID 1022422Notes

Reaction equation

HRID 1022422 reaction equation
[C:1]([O:5][C:6](=[O:39])[C:7]1[CH:19]=[C:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30](=[O:38])[NH:31][CH2:32][CH2:33][CH2:34][C:35]([OH:37])=[O:36])[CH:17]=[C:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[B-](F)(F)(F)F.CN(C(O[N:62]1[C:67](=[O:68])[CH2:66][CH2:65][C:63]1=[O:64])=[N+](C)C)C>C1COCC1>[C:1]([O:5][C:6](=[O:39])[C:7]1[CH:19]=[C:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30](=[O:38])[NH:31][CH2:32][CH2:33][CH2:34][C:35]([O:37][N:62]2[C:67](=[O:68])[CH2:66][CH2:65][C:63]2=[O:64])=[O:36])[CH:17]=[C:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:8]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 684424855-[9-(3-Carboxy-propylcarbamoyl)-nonyloxy]-isophthalic Acid Di-tert-butyl Ester

Product 1

HCID 874559705-{9-[3-(2,5-Dioxo-pyrrolidin-1-yloxycarbonyl)-propylcarbamoyl]-nonyloxy}-isophthalic acid di-tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-[9-(3-Carboxy-propylcarbamoyl)-nonyloxy]-isophthalic acid di-tert-butyl ester (62 mg, 0.11 mmol) in dry THF (2 ml) was added DIPEA (0.05 ml) and TSTU (41 mg, 0.14 mmol). The mixture was stirred at room temperature under nitrogen over night. The mixture was concentrated and EtOAc was added to the residue. The precipitate was removed by filtration. The filtrate was washed with 0.1 N HCl (2×) and brine (1×), dried (Na2SO4) and concentrated to give a clear syrup.

Workup

  1. concentrationThe mixture was concentrated
  2. additionEtOAc was added to the residue
  3. customThe precipitate was removed by filtration
  4. washThe filtrate was washed with 0.1 N HCl (2×) and brine (1×)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customto give a clear syrup

Sources & evidence

ORD record
ord-c8b64bf5562849d58bef4b39a1abe703
Source dataset
uspto-grants-2014_05
Patent number
US08722620B2

Reaction notes

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