Hydrogen Peroxide → HCID 86655971, compound

HRID 1023015Notes

Reaction equation

HRID 1023015 reaction equation
C12BC(CCC1)CCC2.[C:10]([O:14][C:15]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][C@H:22]([NH:30][C:31]([NH:33][C@@H:34]1[CH2:49][C:48]2=[CH:50][CH:51]=[C:45]([CH:46]=[CH:47]2)[O:44][CH2:43][CH:42]=[CH:41][CH2:40][O:39][CH2:38][C@H:37]([CH:52]([CH3:54])[CH3:53])[NH:36][C:35]1=[O:55])=[O:32])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:16])([CH3:13])([CH3:12])[CH3:11].[OH-:56].[Na+].OO>C1COCC1>[C:10]([O:14][C:15]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][C@H:22]([NH:30][C:31]([NH:33][C@@H:34]1[CH2:49][C:48]2=[CH:47][CH:46]=[C:45]([CH:51]=[CH:50]2)[O:44][CH2:43][CH2:42][CH:41]([OH:56])[CH2:40][O:39][CH2:38][C@H:37]([CH:52]([CH3:53])[CH3:54])[NH:36][C:35]1=[O:55])=[O:32])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:16])([CH3:11])([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 86655972HCID 86655972, compound

Product 1

HCID 86655971HCID 86655971, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.55 ml (773 μmol) (0.5M in THF) of 9-borabicyclo[3.3.1]nonane were added to a solution of 50 mg (77 pmol) of tert-butyl(S)-6-tert-butoxycarbonylamino-2-[3-((9S,12R)-9-isopropyl-11-oxo-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1(17),4,14(18),15-tetraen-12-yl)ureido]hexanoate (8-1B) in 1.5 ml of THF, and the mixture was stirred at RT overnight. Addition of 250 μl (1.49 mmol) of 6N sodium hydroxide solution and 207 μl (1.83 mmol) of hydrogen peroxide was followed by extraction with dichloromethane. The organic phase was washed with saturated sodium chloride solution, dried over Na2SO4, filtered and concentrated. The residue was purified by preparative HPLC.

Workup

  1. extractionwas followed by extraction with dichloromethane
  2. washThe organic phase was washed with saturated sodium chloride solution
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-7be87824f6d54ff989e4649b4ecb34af
Source dataset
uspto-grants-2014_05
Patent number
US08722655B2

Reaction notes

Loading…