3-Amino-5-chloro-2-hydroxybenzenesulfonic acid → (2S)-2-amino-4-[(5-chloro-2-hydroxy-3-sulfophenyl)carbamoyl]butanoic acid

HRID 2402922Notes

Reaction equation

HRID 2402922 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.C1C=C2N=NN(O)C2=CC=1.O.C(N=C=NC(C)C)(C)C.[CH:42]1[C:47]([S:48]([OH:51])(=[O:50])=[O:49])=[C:46]([OH:52])[C:45]([NH2:53])=[CH:44][C:43]=1[Cl:54]>CN(C=O)C.C(N(CC)CC)C>[Cl:54][C:43]1[CH:42]=[C:47]([S:48]([OH:51])(=[O:49])=[O:50])[C:46]([OH:52])=[C:45]([NH:53][C:5](=[O:7])[CH2:4][CH2:3][C@@H:2]([C:8]([OH:10])=[O:9])[NH2:1])[CH:44]=1

Participants

7

Reactant 4

HCID 69273-Amino-5-chloro-2-hydroxybenzenesulfonic acidHCID 12734DiisopropylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 6993444(4S)-5-(tert-butoxy)-4-{[(tert-butoxy)carbonyl]amino}-5-oxopentanoic acid

Product 1

HCID 45275684(2S)-2-amino-4-[(5-chloro-2-hydroxy-3-sulfophenyl)carbamoyl]butanoic acidYield 14.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

Boc-Glu-OtBu (100 mg, 0.33 mmol) and HOBt hydrate (65.6 mg, 0.43 mmol) were dissolved in 2 mL of DMF, and triethylamine (0.137 mL) was added thereto. After cooling the mixture down to 0° C., diisopropylcarbodiimide (66.4 μL, 0.43 mmol) and 2-amino-4-chlorophenol-6-sulfonic acid (73.7 mg, 0.33 mmol) were 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 TFA and stirred at room temperature for 2 hours. 2 mL of methylene chloride was added thereto, and a precipitate was taken by filtration to obtain a title compound.

Workup

  1. additionwere added
  2. customAfter removing
  3. customa solvent, purification
  4. dissolutionThe obtained intermediate was dissolved in 2 mL of TFA
  5. stirringstirred at room temperature for 2 hours
  6. addition2 mL of methylene chloride was added
  7. filtrationa precipitate was taken by filtration

Sources & evidence

ORD record
ord-28bab190162d4186a9aa4fc0ca523668
Source dataset
uspto-grants-2014_08
Patent number
US08796485B2

Reaction notes

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