Pyridine → 3-[(4S)-4-amino-5-ethoxy-5-oxopentanamido]-5-chloro-2-hydroxybenzene-1-sulfonic acid

HRID 330872Notes

Reaction equation

HRID 330872 reaction equation
CN(C(ON1N=[N:16][C:11]2[CH:12]=[CH:13][CH:14]=[N:15][C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=NC2N([OH:34])N=NC=2C=1.NC1[C:37]([OH:47])=[C:38]([S:43]([OH:46])(=[O:45])=[O:44])[CH:39]=[C:40]([Cl:42])[CH:41]=1.N1[CH:53]=[CH:52]C=CC=1.[C:54]([OH:60])(C(F)(F)F)=[O:55]>CN(C=O)C>[NH2:16][C@H:11]([C:54]([O:60][CH2:52][CH3:53])=[O:55])[CH2:12][CH2:13][C:14]([NH:15][C:10]1[C:37]([OH:47])=[C:38]([S:43]([OH:46])(=[O:44])=[O:45])[CH:39]=[C:40]([Cl:42])[CH:41]=1)=[O:34]

Participants

7

Reactant 5

HCID 1049PyridineHCID 6422Trifluoroacetic acidHCID 69273-Amino-5-chloro-2-hydroxybenzenesulfonic acidHCID 181649HOAtHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 534690273-[(4S)-4-amino-5-ethoxy-5-oxopentanamido]-5-chloro-2-hydroxybenzene-1-sulfonic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After 92 mg (0.33 mmol) of the compound obtained in Step 1, 130 mg (0.33 mmol) of HATU, 45 mg (0.33 mmol) of HOAt and 77 mg (0.33 mmol) of 3-amino-5-chloro2-hydroxybenzenesulfonic acid were suspended in 1.0 ml of DMF, 0.25 ml of pyridine was added to the suspension. The mixture was stirred at room temperature overnight. The solvent was removed by distillation and the mixture was purified in accordance with the purification step A to give the intermediate. The crude product was dissolved in 4.0 ml of TFA. The solution was stirred at room temperature for an hour. The solvent was removed by distillation and the mixture was purified in accordance with the purification step A to give 47.2 mg of the title compound.

Workup

  1. customThe solvent was removed by distillation
  2. customthe mixture was purified in accordance with the purification step A
  3. customto give the intermediate
  4. stirringThe solution was stirred at room temperature for an hour
  5. customThe solvent was removed by distillation
  6. customthe mixture was purified in accordance with the purification step A

Sources & evidence

ORD record
ord-64343dd915bd4ddc917e9314ddae75ac
Source dataset
uspto-grants-2014_11
Patent number
US08877739B2

Reaction notes

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