Water → HCID 86759953, compound

HRID 1242056Notes

Reaction equation

HRID 1242056 reaction equation
[C:1]([O:5][C:6](=[O:28])[C:7]([O:9][CH2:10][CH:11]1[O:16][CH2:15][C:14]2[S:17][C:18]([NH2:27])=[C:19]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:13]=2[CH2:12]1)=[O:8])(C)(C)C.C(=O)([O-])[O-].[K+].[K+].O>CO>[CH3:1][O:5][C:6](=[O:28])[C:7]([O:9][CH2:10][CH:11]1[O:16][CH2:15][C:14]2[S:17][C:18]([NH2:27])=[C:19]([C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])[C:13]=2[CH2:12]1)=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 86759954HCID 86759954, compound

Product 1

HCID 86759953HCID 86759953, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the above oxalic acid 2-amino-3-tert-butoxycarbonyl-4,7-dihydro-5H-thieno[2,3-c]pyran-5-ylmethyl ester tert-butyl ester (8.3 g, 20.1 mmol) and potassium carbonate (1.7 g, 12.3 mmol) was stirred in methanol (80 ml) in presence of water (3 ml) at room temperature for 10 min., at which time TLC indicated reaction complete. Methanol was removed in vacuo and the crude product was dissolved in dichloromethane (300 ml) and washed with water (3×150 ml). The organic phase was dried (MgSO4), filtered and the solvent evaporated in vacuo. The residue was purified on flash chromatography on silica gel using a gradient of hexane/ethyl acetate (90:10 to 50:50 gradient) as eluant. Pure fractions were collected and the solvent evaporated in vacuo affording 0.65 g (9%) of oxalic acid 2-amino-3-tert-butoxycarbonyl-4,7-dihydro-5H-thieno[2,3-c]pyran-5-ylmethyl ester methyl ester as a solid.

Workup

  1. customreaction complete
  2. customMethanol was removed in vacuo
  3. dissolutionthe crude product was dissolved in dichloromethane (300 ml)
  4. washwashed with water (3×150 ml)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent evaporated in vacuo
  8. customThe residue was purified on flash chromatography on silica gel using a gradient of hexane/ethyl acetate (90:10 to 50:50 gradient) as eluant
  9. customPure fractions were collected
  10. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-ab8c7ecef6454a4b98263c225ca25327
Source dataset
uspto-grants-2006_10
Patent number
US07115624B1

Reaction notes

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