Acetic Acid → HCID 69739503, compound

HRID 1384863Notes

Reaction equation

HRID 1384863 reaction equation
[C:1]([OH:4])(=O)[CH3:2].[C:5]([O:9][C:10]([C:12]1[C:20]2[CH2:19][CH:18]([CH2:21][NH2:22])[O:17][CH2:16][C:15]=2[S:14][C:13]=1[NH2:23])=[O:11])([CH3:8])([CH3:7])[CH3:6]>C(#N)C>[C:5]([O:9][C:10]([C:12]1[C:20]2[CH2:19][CH:18]([CH2:21][N:22]3[CH2:16][C:15]4[C:2](=[CH:21][CH:18]=[CH:19][CH:20]=4)[C:1]3=[O:4])[O:17][CH2:16][C:15]=2[S:14][C:13]=1[NH2:23])=[O:11])([CH3:8])([CH3:6])[CH3:7]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 54228347HCID 54228347, compound

Product 1

HCID 69739503HCID 69739503, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Phthalic dicarboxaldehyde (52 mg, 0.36 mmol) was dissolved in a mixture of anhydrous acetonitrile (2 ml) and acetic acid (44 μl, 0.72 mmol). The above 2-amino-5-aminomethyl-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester (0.11 g, 0.36 mmol) was added and the reaction stirred for 20 minutes at room temperature. The volatiles were evaporated in vacuo and the residue dissolved in ethyl acetate (25 ml). The organic mixture was washed with saturated sodium bicarbonate (5 ml), 1% hydrochloric acid (5 ml), brine (5 ml), dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by chromatography using a gradient from 15% ethyl acetate/dichloromethane to 17% ethyl acetate/dichloromethane as eluent affording 45 mg (30%) of 2-amino-5-(1-oxo-1,3-dihydro-isoindol-2-ylmethyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester as a solid.

Workup

  1. customThe volatiles were evaporated in vacuo
  2. dissolutionthe residue dissolved in ethyl acetate (25 ml)
  3. washThe organic mixture was washed with saturated sodium bicarbonate (5 ml), 1% hydrochloric acid (5 ml), brine (5 ml)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-57fb5a1e67204f4b9a3b73c0755dbc63
Source dataset
uspto-grants-2001_07
Patent number
US06262044B1

Reaction notes

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