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

HRID 705459Notes

Reaction equation

HRID 705459 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+].[NH:16](C(OC(C)(C)C)=O)[C@H:17]([C:23]([O:25]C(C)(C)C)=[O:24])[CH2:18][CH2:19][C:20](=O)[OH:21].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:20](=[O:21])[CH2:19][CH2:18][C@@H:17]([C:23]([OH:25])=[O:24])[NH2:16]

Participants

10

Reactant 5

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 hydrochloride

Product 1

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

Reagents, catalysts & solvents 4

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

Procedure

2 mL of methanol and 3 mL of water were added to sodium 4-chloro-3-nitrobenzenesulfonate (1 mmol). 2% Pt-S/C in catalyst quantity was added thereto and stirred under hydrogen atmosphere overnight at room temperature. After filtering out the catalyst, the mixture was sufficiently dried. Then, 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 thereto and stirred at room temperature overnight. The reaction solution was diluted with water-acetonitrile and purified in accordance with the purification process A to obtain a protected form of a title compound. The obtained protected form was dissolved in 3 mL of a trifluoroacetic acid and stirred at room temperature for 2 hours. After removing a solvent, purification was conducted in accordance with the purification process A to obtain a title compound.

Workup

  1. filtrationAfter filtering out the catalyst
  2. customthe mixture was sufficiently dried
  3. stirringstirred at room temperature overnight
  4. custompurified in accordance with the purification process

Sources & evidence

ORD record
ord-5719e04f47854dcd8908f4e6b35a866e
Source dataset
uspto-grants-2015_11
Patent number
US09174932B2

Reaction notes

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