Acetic Acid → HCID 69739503, compound

HRID 2187910Notes

Reaction equation

HRID 2187910 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 acetateldichloromethane 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-353966c5095241f09344fdd8361717b9
Source dataset
uspto-grants-2002_06
Patent number
US06410586B1

Reaction notes

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