Benzyl Bromide → HCID 10813914, compound

HRID 1532032Notes

Reaction equation

HRID 1532032 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:15][C:16]1[C:17]([OH:26])=[N:18][O:19][C:20]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:33](Br)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CC(C)=O>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:15][C:16]1[C:17]([O:26][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[N:18][O:19][C:20]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3].[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:15][C:16]1[C:17](=[O:26])[N:18]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:19][C:20]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178470547HCID 178470547, compound

Product 2

HCID 10790222HCID 10790222, compoundYield 18%HCID 10813914HCID 10813914, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of ethyl (RS)-2-tert-butoxycarbonylamino-3-(5-ethoxycarbonyl-3-hydroxyisoxazol-4-yl)propionate (3.2 g, 8.6 mmol), K2CO3 (2.4 g, 17.2 mmol) in acetone (40 mL) was heated to reflux temperature. Benzyl bromide (2.2 g, 12.9 mmol) was added, and the mixture was boiled under reflux for 1.5 h. Concentrated in vacuo and subjected to flash chromatography (SiO2, eluent: heptane/ethyl acetate (2:1)) to give ethyl (RS)-2-[(tert-butoxycarbonyl)amino]-3-[3-benzyloxy-5-(ethoxycarbonyl)isoxazol-4-yl]propionate (1.64 g, 41%) and ethyl (RS)-2-[(tert-butoxycarbonyl)amino]-3-(2-benzyl-5-ethoxycarbonyl-2,3-dihydro-3-oxoisoxazol-4-yl)propionate (0.7 g, 18%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux temperature
  3. temperatureunder reflux for 1.5 h
  4. concentrationConcentrated in vacuo

Sources & evidence

ORD record
ord-fbcead47655d4c3e859cd11da139e540
Source dataset
uspto-grants-2001_03
Patent number
US06200999B1

Reaction notes

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