Sodium Hydroxide → HCID 66625195, compound

HRID 416526Notes

Reaction equation

HRID 416526 reaction equation
C(OC(=O)[NH:10][C@@H:11]([CH2:26][O:27]CC1C=CC=CC=1)[CH2:12][S:13](=[O:25])(=[O:24])[NH:14][CH:15]1[CH2:20][CH2:19][N:18]([CH:21]([CH3:23])[CH3:22])[CH2:17][CH2:16]1)C1C=CC=CC=1.B(Br)(Br)Br.[OH-].[Na+]>ClCCl.O>[CH:21]([N:18]1[CH2:17][CH2:16][CH:15]([NH:14][S:13]([CH2:12][C@@H:11]([NH2:10])[CH2:26][OH:27])(=[O:25])=[O:24])[CH2:20][CH2:19]1)([CH3:23])[CH3:22]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 66624637HCID 66624637, compound

Product 1

HCID 66625195HCID 66625195, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6344DichloromethaneSolvent2×

Procedure

80 mg (0.16 mmol) [(S)-1-Benzyloxymethyl-2-(1-isopropyl-piperidin-4-ylsulfamoyl)-ethyl]-carbamic acid benzyl ester were dissolved in 3 ml dichloromethane. At 0° C., 0.32 ml of a 1 M BBr3-solution in dichloromethane were added and the reaction mixture was allowed to warm to room temperature. After 24 h a few drops of water and 0.94 ml of a 1 M aqueous NaOH-solution were added. The mixture was concentrated under reduced pressure. The residue was taken up in DMF and filtered in order to get rid of salts. The filtrate was concentrated under vacuo to give crude (S)-2-amino-3-hydroxy-propane-1-sulfonic acid (1-isopropyl-piperidin-4-yl)-amide, which was pure enough for further transformations. Yield:

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. filtrationfiltered in order
  3. customto get rid of salts
  4. concentrationThe filtrate was concentrated under vacuo

Sources & evidence

ORD record
ord-430df0a8ce9147d8882f75a29a8a8630
Source dataset
uspto-grants-2012_01
Patent number
US08088925B2

Reaction notes

Loading…