Water → HCID 178454094, compound

HRID 624271Notes

Reaction equation

HRID 624271 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:12][C@H:11]([C:13]([OH:15])=[O:14])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:10][C@H:11]([C:13]([O:15][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:14])[CH2:12]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178454093HCID 178454093, compound

Product 1

HCID 178454094HCID 178454094, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of trans-3-(tert-butoxycarbonylamino)cyclobutanecarboxylic acid (0.5 g, 2.323 mmol) and potassium carbonate (0.321 g, 2.323 mmol) in dimethylformamide (2.323 ml) was treated with (bromomethyl)benzene (0.401 g, 2.346 mmol) added from a syringe over 3 minutes. The reaction mixture was stirred at room temperature for 17 hours and water was added. The suspension was filtered and the solid collected was washed with water and dried under vacuum to give the title compound.

Workup

  1. additionadded from a syringe over 3 minutes
  2. filtrationThe suspension was filtered
  3. customthe solid collected
  4. washwas washed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-0aa01e2293fb474899234f2d1c703a50
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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