Isopropanol → HCID 59190395, compound

HRID 219610Notes

Reaction equation

HRID 219610 reaction equation
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[Br:14][C:15]1[CH:20]=[CH:19][C:18]([C@@H:21]([N:23]2[CH2:29][CH2:28][CH2:27][C@:26]([CH2:36][CH2:37][CH2:38][OH:39])([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[NH:25][C:24]2=[O:40])[CH3:22])=[CH:17][CH:16]=1.CC(O)C>CC(C)=O>[Br:14][C:15]1[CH:20]=[CH:19][C:18]([C@@H:21]([N:23]2[CH2:29][CH2:28][CH2:27][C@:26]([CH2:36][CH2:37][C:38]([OH:3])=[O:39])([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[NH:25][C:24]2=[O:40])[CH3:22])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 59190366HCID 59190366, compoundHCID 131709961Jones' reagent

Product 1

HCID 59190395HCID 59190395, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A stirred mixture of Jones reagent (0.25 mL) and acetone (2 mL) was cooled in an ice bath and a solution of (S)-1-((S)-1-(4-bromophenyl)ethyl)-4-(3-hydroxypropyl)-4-phenyl-1,3-diazepan-2-one (45 mg, 0.11 mmol) in acetone (6 mL) was added dropwise over 10 min The mixture was stirred in the ice bath for 2 h and i-PrOH (2 mL) was added. The mixture was concentrated under reduced pressure. The residue was taken up in EtOAc (100 mL), washed with water (15 mL) and brine (15 mL), and dried over Na2SO4. Removal of the solvent afforded crude 3-((S)-1-((S)-1-(4-bromophenyl)ethyl)-2-oxo-4-phenyl-1,3-diazepan-4-yl)propanoic acid (33 mg, 69%) which was used without further purification.

Workup

  1. temperaturewas cooled in an ice bath
  2. concentrationThe mixture was concentrated under reduced pressure
  3. washwashed with water (15 mL) and brine (15 mL)
  4. dry with materialdried over Na2SO4
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-2d5a51f349154ef295b541e82da12138
Source dataset
uspto-grants-2012_06
Patent number
US08202857B2

Reaction notes

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