Water → HCID 86723563, compound

HRID 2201657Notes

Reaction equation

HRID 2201657 reaction equation
[CH2:1]=[C:2]1[CH2:5][CH:4]([CH2:6][NH2:7])[CH2:3]1.C([O-])([O-])=O.[Na+].[Na+].Cl[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].O>O1CCCC1>[CH2:1]=[C:2]1[CH2:5][CH:4]([CH2:6][NH:7][C:15](=[O:16])[O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 177500821-(3-Methylidenecyclobutyl)methanamine

Product 1

HCID 86723563HCID 86723563, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 4-2 (3 g, 30.9 mmol) was dissolved in 50 mL of tetrahydrofuran, added Na2CO3 (6.3 g, 60 mmol) and benzyl chloroformate (5.25 g, 30.8 mmol). The mixture was stirred for 12 hours at room temperature, added 100 mL of water, extracted three times with 300 mL of ethyl acetate, combined the organic phases, rotary evaporated to remove solvents and purified by column chromatography (petroleum ether/ethyl acetate=10:1) to give Compound 4-3 (4 g, 56% yield).

Workup

  1. extractionextracted three times with 300 mL of ethyl acetate
  2. customrotary evaporated
  3. customto remove solvents
  4. custompurified by column chromatography (petroleum ether/ethyl acetate=10:1)

Sources & evidence

ORD record
ord-eef0e8133ab7412380e1dd79abf4ccb8
Source dataset
uspto-grants-2016_06
Patent number
US09365499B2

Reaction notes

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