3-Aminobenzenesulfonic acid → N5-(3-sulfophenyl)-L-glutamine

HRID 705444Notes

Reaction equation

HRID 705444 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:8]([O:10]C(C)(C)C)=[O:9])[CH2:3][CH2:4][C:5](=[O:7])O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=NC2N(O)N=NC=2C=1.[S:56]([C:60]1[CH:61]=[C:62]([CH:64]=[CH:65][CH:66]=1)[NH2:63])([OH:59])(=[O:58])=[O:57]>CN(C=O)C.C(N(CC)CC)C>[S:56]([C:60]1[CH:61]=[C:62]([NH:63][C:5](=[O:7])[CH2:4][CH2:3][C@@H:2]([C:8]([OH:10])=[O:9])[NH2:1])[CH:64]=[CH:65][CH:66]=1)([OH:59])(=[O:58])=[O:57]

Participants

7

Reactant 4

HCID 84743-Aminobenzenesulfonic acidHCID 181649HOAtHCID 6993444(4S)-5-(tert-butoxy)-4-{[(tert-butoxy)carbonyl]amino}-5-oxopentanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 45275583N5-(3-sulfophenyl)-L-glutamineYield 41%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

Boc-Glu-OtBu (75 mg, 0.247 mmol), HATU (112 mg, 0.296 mmol) and HOAt (41 mg, 0.296 mmol) were dissolved in 1 mL of DMF. Triethylamine (52 μL) was added thereto and stirred at room temperature for 10 minutes. 3-Sulfoaniline (43 mg, 0.247 mmol) was added thereto and stirred overnight at room temperature. After removing a solvent, purification was conducted in accordance with the purification process A. The obtained intermediate was dissolved in 2 mL of a trifluoroacetic acid and stirred at room temperature for 3 hours, and a solvent was removed therefrom. The obtained product was purified in accordance with the purification process A to obtain a title compound.

Workup

  1. stirringstirred overnight at room temperature
  2. customAfter removing
  3. customa solvent, purification
  4. dissolutionThe obtained intermediate was dissolved in 2 mL of a trifluoroacetic acid
  5. stirringstirred at room temperature for 3 hours
  6. customa solvent was removed
  7. customThe obtained product was purified in accordance with the purification process

Sources & evidence

ORD record
ord-8ceaf5f76a064b27b82d1091b9088b5e
Source dataset
uspto-grants-2015_11
Patent number
US09174932B2

Reaction notes

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