3-Methoxyaniline → HCID 22501705, compound

HRID 1813889Notes

Reaction equation

HRID 1813889 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([NH2:9])[CH:4]=1.[CH3:10][C:11]([O:14][C:15]([NH:17][C@@H:18]1[C:21](=[O:22])[O:20][CH2:19]1)=[O:16])([CH3:13])[CH3:12]>C1COCC1>[OH:22][CH2:21][CH:18]([NH:17][C:15](=[O:16])[O:14][C:11]([CH3:12])([CH3:10])[CH3:13])[C:19]([NH:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:20]

Participants

4

Reactant 2

HCID 108243-MethoxyanilineHCID 2763194tert-Butyl [(3S)-2-oxooxetan-3-yl]carbamate

Product 1

HCID 22501705HCID 22501705, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of m-anisidine (171 mg, 1.38 mmol) in THF (30 ml), N-(tert-butoxycarbonyl)-L-serine β-lactone (200 mg, 1.06 mmol) was added, and the mixture was refluxed overnight under argon. The reaction mixture was concentrated on a rotary evaporator. The residue was subjected to flash column chromatography, eluting with EtOAc/hexanes of various compositions.

Workup

  1. temperaturethe mixture was refluxed overnight under argon
  2. concentrationThe reaction mixture was concentrated on a rotary evaporator
  3. washeluting with EtOAc/hexanes of various compositions

Sources & evidence

ORD record
ord-466eff6806e449e785e962e6544c27f2
Source dataset
uspto-grants-2005_04
Patent number
US06875757B2

Reaction notes

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