Hydrogen Peroxide → HCID 86635950, compound

HRID 561895Notes

Reaction equation

HRID 561895 reaction equation
[CH2:1]([C:4]1[CH:49]=[C:48]([Cl:50])[C:7]([O:8][CH2:9][CH2:10][O:11][C:12]2[CH:47]=[CH:46][C:15]([CH2:16][CH:17]([C:27]([N:29]([CH2:33][C:34]3[CH:39]=[C:38]([CH2:40][CH2:41][CH2:42][O:43][CH3:44])[CH:37]=[CH:36][C:35]=3[Cl:45])[CH:30]3[CH2:32][CH2:31]3)=[O:28])[CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:14][CH:13]=2)=[C:6]([Cl:51])[CH:5]=1)[CH:2]=[CH2:3].C12BC(CCC1)CCC2.[OH-:61].[Na+].OO>CCOC(C)=O.C1COCC1>[Cl:45][C:35]1[CH:36]=[CH:37][C:38]([CH2:40][CH2:41][CH2:42][O:43][CH3:44])=[CH:39][C:34]=1[CH2:33][N:29]([CH:30]1[CH2:32][CH2:31]1)[C:27](=[O:28])[CH:17]([CH2:16][C:15]1[CH:14]=[CH:13][C:12]([O:11][CH2:10][CH2:9][O:8][C:7]2[C:6]([Cl:51])=[CH:5][C:4]([CH2:1][CH2:2][CH2:3][OH:61])=[CH:49][C:48]=2[Cl:50])=[CH:47][CH:46]=1)[CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:25])[CH3:24]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 86635951HCID 86635951, compound

Product 1

HCID 86635950HCID 86635950, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a THF solution (0.04 M) of tert-butyl {2-{4-[2-(4-allyl-2,6-dichlorophenoxy)ethoxy]benzyl}-3-[[2-chloro-5-(3-methoxypropyl)benzyl](cyclopropyl)amino]-3-oxopropyl)carbamate from Example 122, Step 5 (1 eq.) was added 9-borabicyclo[3.3.1]nonane (0.5 M THF solution, 2.6 eq.) dropwise at 0° C. The resulting solution was warmed slowly to RT over 16 h. The reaction was quenched at 0° C. with the dropwise addition of ethanol. Then, NaOH (1 N aqueous solution, 4 eq.) and H2O2 (30% w/w aqueous solution, 12 eq.) were added. After 1 h of stirring at 0° C. and another 4 h of stirring at RT, the reaction mixture was diluted with EtOAc. The organic layer was separated, washed with water, dried over Na2SO4 and filtered. Concentration of the filtrate in vacuo and purification of the crude product thus obtained by way of flash chromatography (SiO2, 3:1 (v/v) Hex:EtOAc→EtOAc), revealed the title compound.

Workup

  1. customThe reaction was quenched at 0° C. with the dropwise addition of ethanol
  2. stirringof stirring at RT
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customConcentration of the filtrate in vacuo and purification of the crude product
  8. customthus obtained by way of flash chromatography (SiO2, 3:1 (v/v) Hex:EtOAc→EtOAc)

Sources & evidence

ORD record
ord-913497c2b71a45fd843b4f98a5a6b79c
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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