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

HRID 1773099Notes

Reaction equation

HRID 1773099 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)[OH:6].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.[NH2:56][C:57]1[C:58]([OH:68])=[C:59]([S:64]([OH:67])(=[O:66])=[O:65])[CH:60]=[C:61]([Cl:63])[CH:62]=1>CN(C=O)C.C(O)(C(F)(F)F)=O.N1C=CC=CC=1>[NH2:1][C@@H:2]([CH2:3][CH2:4][C:5](=[O:6])[NH:56][C:57]1[CH:62]=[C:61]([Cl:63])[CH:60]=[C:59]([S:64]([OH:67])(=[O:66])=[O:65])[C:58]=1[OH:68])[C:8]([OH:10])=[O:9]

Participants

8

Reactant 4

HCID 69273-Amino-5-chloro-2-hydroxybenzenesulfonic 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 45275684(2S)-2-amino-4-[(5-chloro-2-hydroxy-3-sulfophenyl)carbamoyl]butanoic acid

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

101 mg (0.33 mmol) of Boc-Glu-OtBu, 130 mg (0.33 mmol) of HATU, 45 mg (0.33 mmol) of HOAt and 77 mg (0.33 mmol) of 3-amino-5-chloro-2-hydroxybenzenesulfonic acid were suspended in 2.0 ml of DMF, to which 0.5 ml of pyridine was added and stirred at room temperature overnight. After distilling the solvent away, purification step A was used to obtain an intermediate. This crude product was dissolved in 2.0 ml of TFA and stirred at room temperature for 90 minutes. After distilling the solvent away, purification step A was used to obtain the title compound.

Workup

  1. additionwas added
  2. distillationAfter distilling the solvent away
  3. custompurification step A
  4. customto obtain an intermediate
  5. stirringstirred at room temperature for 90 minutes
  6. distillationAfter distilling the solvent away
  7. custompurification step A

Sources & evidence

ORD record
ord-6a89b4f0b068462d8f597b94806ecac8
Source dataset
uspto-grants-2016_02
Patent number
US09253997B2

Reaction notes

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