Hydrochloric Acid → (S)-2-Benzenesulfonylamino-9-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-nonanoic acid

HRID 1837901Notes

Reaction equation

HRID 1837901 reaction equation
[NH2:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[CH2:19][CH2:18][CH2:17][NH:16][C:15]=2[N:14]=1)[C:3]([OH:5])=[O:4].[OH-].[Na+].[C:25]1([S:31](Cl)(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.Cl>O.O1CCOCC1.O1CCOCC1>[C:25]1([S:31]([NH:1][C@@H:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]2[CH:22]=[CH:21][C:20]3[CH2:19][CH2:18][CH2:17][NH:16][C:15]=3[N:14]=2)[C:3]([OH:5])=[O:4])(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7369Benzenesulfonyl chlorideHCID 14798Sodium Hydroxide2×HCID 226781442-Amino-9-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-nonanoic acid

Product 1

HCID 21967992(S)-2-Benzenesulfonylamino-9-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-nonanoic acid

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A solution of 13-9 (0.27 g, 0.88 mmol) in H2O/dioxane (2:1, 4.4 mL) was cooled to 0° C. and then treated dropwise with 1N NaOH to attained a pH of 10.5. The reaction mixture was then treated with with PhSO2Cl (0.23 g, 1.3 mmol) in dioxane (750 μL) while maintaining a pH of 10.5 by adding 1N NaOH. After 15 min, the pH was adjusted to 7 with 1N HCl to effect a white precipitate. The precipitate was collected by filtration and triturated with EtOAc and then ether to give 13-10 as a colorless solid.

Workup

  1. temperaturewhile maintaining a pH of 10.5
  2. filtrationThe precipitate was collected by filtration
  3. customtriturated with EtOAc

Sources & evidence

ORD record
ord-c220d3ec50a641cea6367b25cd435cf3
Source dataset
uspto-grants-2004_08
Patent number
US06784190B2

Reaction notes

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