Benzoyl chloride → HCID 86648967, compound

HRID 449934Notes

Reaction equation

HRID 449934 reaction equation
[OH:1][CH:2]1[CH2:5][CH:4]([NH:6][C:7](=[O:9])[OH:8])[CH2:3]1.[C:10](Cl)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>N1C=CC=CC=1>[C:11]([O:9][C:7]([NH:6][CH:4]1[CH2:5][CH:2]([O:1][C:10](=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:3]1)=[O:8])([CH3:16])([CH3:12])[CH3:10]

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 57486966HCID 57486966, compound

Product 1

HCID 86648967HCID 86648967, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of (3-hydroxycyclobutyl)carbamic acid tent-butyl ester (180 mg, 0.96 mmol) in pyridine (4 mL) was added benzoyl chloride (116 μL, 1.0 mmol). The reaction mixture was stirred at room temperature for 2 hrs and then concentrated under reduced pressure. The residue was dissolved in EtOAc (20 mL), washed with 1 N HCl, water and brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Et2O/pentane: gradient 0% to 50%) to give benzoic acid 3-tert-butoxycarbonylaminocyclobutyl ester as a white solid (262 mg, yield: 94%). LCMS (ESI) m/z: 192 [M+H-BOC]+

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc (20 mL)
  3. washwashed with 1 N HCl, water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (Et2O/pentane: gradient 0% to 50%)

Sources & evidence

ORD record
ord-1788fc2a670d4e8e8b3023fa77ef3b2e
Source dataset
uspto-grants-2013_07
Patent number
US08486950B2

Reaction notes

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