Diisopropylethylamine → N5-(2-chloro-5-sulfophenyl)-L-glutamine

HRID 330868Notes

Reaction equation

HRID 330868 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O-:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-])=O.[Na+].[H][H].[NH:18](C(OC(C)(C)C)=O)[C@H:19]([C:25]([O:27]C(C)(C)C)=[O:26])[CH2:20][CH2:21][C:22](=O)[OH:23].Cl.C1C=NC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>O.C(#N)C.CN(C=O)C.O.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[NH:12][C:22](=[O:23])[CH2:21][CH2:20][C@@H:19]([C:25]([OH:27])=[O:26])[NH2:18]

Participants

11

Reactant 6

HCID 81531DiisopropylethylamineHCID 87246Benzenesulfonic acid, 4-chloro-3-nitro-, sodium salt (1:1)HCID 181649HOAtHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 131731743Boc-Glu-OtBu hydrochlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 131731744N5-(2-chloro-5-sulfophenyl)-L-glutamine

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To sodium 4-chloro-3-nitrobenzenesulfonate (1 mmol) were added 2 ml of methanol and 3 ml of water. A catalytic amount of 2% Pt-S/C was added to the mixture, followed by stirring at room temperature overnight in a hydrogen atmosphere. The catalyst was removed by filtration. After thoroughly drying, 303 mg (1 mmol) of Boc-Glu-OtBu hydrochloride, 163 mg (1.2 mmol) of HOAt, 456 mg (1.2 mmol) of HATU, 2 ml of DMF and 0.35 ml of DIEA were added and stirred at room temperature overnight. The reaction solution was diluted in water-acetonitrile and purified according to the purification step A to give the protected form of the title compound. The resulting protected product was dissolved in 3 ml of trifluoroacetic acid and stirred at room temperature for 2 hours. The solvent was then removed by distillation. The mixture was purified according to the purification step A to give the title compound.

Workup

  1. customThe catalyst was removed by filtration
  2. customAfter thoroughly drying
  3. custompurified
  4. customaccording to the purification step A

Sources & evidence

ORD record
ord-f4ac48fcb55e4b878b33aaa34ec57f14
Source dataset
uspto-grants-2014_11
Patent number
US08877739B2

Reaction notes

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