Tetrahydrofuran → tert-butyl N-(5-formyl-1,3-thiazol-2-yl)carbamate

HRID 1818954Notes

Reaction equation

HRID 1818954 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[S:9][C:10]([CH2:13][OH:14])=[CH:11][N:12]=1)([CH3:4])([CH3:3])[CH3:2].C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-][Cr](O[Cr]([O-])(=O)=O)(=O)=O.C1COCC1>ClCCl>[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[S:9][C:10]([CH:13]=[O:14])=[CH:11][N:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724130Cornforth reagent2×HCID 53397352Tert-butyl 5-(hydroxymethyl)thiazol-2-ylcarbamate

Product 1

HCID 53393345tert-butyl N-(5-formyl-1,3-thiazol-2-yl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 62.2 (18.5 mmol) in dichloromethane is added molecular sieves (4.0 g) and PDC (39.0 mmol) at room temperature (THF is added to help dissolve the starting material). After 1.5 hours, an additional equivalent of PDC is added and the reaction is stirred for 5.5 hours. The reaction mixture is poured directly onto a silica gel column and is eluted with a gradient of 100% dichloromethane to 100% EtOAc. Fractions containing the desired product are pooled and concentrated to afford (5-formyl-thiazol-2-yl)-carbamic acid tert-butyl ester (compound 62.3).

Workup

  1. additionis added
  2. dissolutionto help dissolve the starting material)
  3. additionThe reaction mixture is poured directly onto a silica gel column
  4. washis eluted with a gradient of 100% dichloromethane to 100% EtOAc
  5. additionFractions containing the desired product
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6c5cab683b3c441fbfc686c9d6fa5311
Source dataset
uspto-grants-2009_10
Patent number
US07601725B2

Reaction notes

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