Sodium Hydroxide → HCID 66624958, compound

HRID 416539Notes

Reaction equation

HRID 416539 reaction equation
C([O:8][C:9](=[O:37])[CH2:10][CH:11]([S:24](=[O:36])(=[O:35])[NH:25][CH:26]1[CH2:31][CH2:30][N:29]([CH:32]([CH3:34])[CH3:33])[CH2:28][CH2:27]1)[CH2:12][NH:13]C(OCC1C=CC=CC=1)=O)C1C=CC=CC=1.B(Br)(Br)Br.[OH-].[Na+]>ClCCl.O>[NH2:13][CH2:12][CH:11]([S:24](=[O:36])(=[O:35])[NH:25][CH:26]1[CH2:27][CH2:28][N:29]([CH:32]([CH3:34])[CH3:33])[CH2:30][CH2:31]1)[CH2:10][C:9]([OH:37])=[O:8]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 66625007HCID 66625007, compound

Product 1

HCID 66624958HCID 66624958, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6344DichloromethaneSolvent2×

Procedure

24 mg (0.04 mmol) 4-Benzyloxycarbonylamino-3-(1-isopropyl-piperidin-4-ylsulfamoyl)-butyric acid benzyl ester were dissolved in 3 ml dichloromethane. At 0° C., 0.1 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 0.3 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 4-amino-3-(1-isopropyl-piperidin-4-ylsulfamoyl)-butyric acid, which was pure enough for further transformations. Yield: 14 mg

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-b0aa69c129e94f82a3f8efefc4d33ed2
Source dataset
uspto-grants-2012_01
Patent number
US08088925B2

Reaction notes

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