2-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate → HCID 87307863, compound

HRID 2361844Notes

Reaction equation

HRID 2361844 reaction equation
[C:1]([O:5][C:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([NH:28][CH2:29][CH:30]1[CH2:35][CH2:34][CH:33]([C:36]([OH:38])=[O:37])[CH2:32][CH2:31]1)=[O:27])=[O:7])([CH3:4])([CH3:3])[CH3:2].[B-](F)(F)(F)F.CN(C(O[N:52]1[C:57](=[O:58])[CH2:56][CH2:55][C:53]1=[O:54])=[N+](C)C)C>C1COCC1.C(#N)C>[O:54]=[C:53]1[CH2:55][CH2:56][C:57](=[O:58])[N:52]1[O:37][C:36]([CH:33]1[CH2:34][CH2:35][CH:30]([CH2:29][NH:28][C:26](=[O:27])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:31][CH2:32]1)=[O:38]

Participants

5

Reactant 2

HCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 67201979HCID 67201979, compound

Product 1

HCID 87307863HCID 87307863, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[(19-tert-butoxycarbonylnonadecanoylamino)methyl]cyclohexanecarboxylic acid (5.56 g) in THF (100 ml) was added a solution of TSTU (3.42 g) in acetonitrile (25 ml). The mixture was concentrated in vacuo after stirring over night. The solid residue was recrystallized from acetonitrile to give 4-[(19-tert-butoxycarbonylnonadecanoylamino)methyl]cyclohexanecarboxylic acid 2,5-dioxopyrrolidin-1-yl ester (5.76 g, 88%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe solid residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-d7b74f28abe64ad2a90d5c73bf47153a
Source dataset
uspto-grants-2014_04
Patent number
US08691759B2

Reaction notes

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