p-Toluenesulfonic acid → 3,3-Dimethoxy-4-benzyloxycarbonylamino-tetrahydrofuran

HRID 413230Notes

Reaction equation

HRID 413230 reaction equation
CO[CH:3]([O:6][CH3:7])[O:4][CH3:5].[CH2:8]([O:15][C:16]([NH:18][CH:19]1[CH2:23][O:22][CH2:21]C1=O)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CC1C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:7][O:6][C:3]1([O:4][CH3:5])[CH:19]([NH:18][C:16]([O:15][CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[O:17])[CH2:23][O:22][CH2:21]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 18523485Benzyl (4-oxotetrahydrofuran-3-yl)carbamate

Product 1

HCID 185234863,3-Dimethoxy-4-benzyloxycarbonylamino-tetrahydrofuran

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Trimethylorthoformate (29 ml) was added dropwise to a refluxing solution of 4-benzyloxycarbonylamino-tetrahydrofuran-3-one (18 g, 78 mmol) and PTSA (500 mg) in MeOH (100 ml). After 3 hours, the reaction mixture was filtered and concentrated to afford, after column chromatography, the title compound as a yellow oil, 16.2 g, 76%.

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationconcentrated
  3. customto afford

Sources & evidence

ORD record
ord-3d9832a0659e4d9e8f4e2e1c7e6193da
Source dataset
uspto-grants-2003_05
Patent number
US06566373B2

Reaction notes

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