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Diisopropylethylamine → HCID 87218236, compound

HRID 593235
Notes
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Reaction equation

HRID 593235 reaction equation
[O:1]=[C:2]1[CH:6]=[CH:5][C:4](=[O:7])[N:3]1[CH2:8][CH2:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[O:11].[B-](F)(F)(F)F.CN(C(O[N:36]1[C:41](=[O:42])[CH2:40][CH2:39][C:37]1=[O:38])=[N+](C)C)C.CCN(C(C)C)C(C)C>C1COCC1>[O:38]=[C:37]1[CH2:39][CH2:40][C:41](=[O:42])[N:36]1[O:21][C:20](=[O:22])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][NH:12][C:10](=[O:11])[CH2:9][CH2:8][N:3]1[C:4](=[O:7])[CH:5]=[CH:6][C:2]1=[O:1]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 66968126Octanoic acid, 8-[[3-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxopropyl]amino]-

Product 1

HCID 87218236HCID 87218236, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a solution of 8-[3-(2,5-dioxo-2,5-dihydropyrrol-1-yl)propionylamino]octanoic acid (917 mg, crude) in dry THF (15 ml) was added TSTU (1.07 mg) and DIPEA (0.65 ml). The mixture was stirred under nitrogen over night. The mixture was concentrated. To the residue was added EtOAc and the precipitate was filtered off. The filtrate was extracted with 0.1 N HCl (2×) and brine (1×), dried (Na2SO4) and concentrated to give an off-white solid. Overall yield 37% (444 mg). LC-MS, M/z: 408.39 (M+1).

Workup

  1. concentrationThe mixture was concentrated
  2. additionTo the residue was added EtOAc
  3. filtrationthe precipitate was filtered off
  4. extractionThe filtrate was extracted with 0.1 N HCl (2×) and brine (1×)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customto give an off-white solid

Sources & evidence

ORD record
ord-647f5ccc58084c96951afa7f6d2c4522
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09242011B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes