Diisopropylcarbodiimide → HCID 69585728, compound

HRID 1242050Notes

Reaction equation

HRID 1242050 reaction equation
[C:1]([O:5][C:6]([C:8]1[C:16]2[CH2:15][CH:14]([CH2:17][NH2:18])[O:13][CH2:12][C:11]=2[S:10][C:9]=1[NH2:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N+:20]([C:23]1[CH:24]=[C:25]([C:32](O)=[O:33])[C:26](=[CH:30][CH:31]=1)[C:27](O)=[O:28])([O-:22])=[O:21].C(N(C(C)C)CC)(C)C.C(N=C=NC(C)C)(C)C>O1CCCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([C:8]1[C:16]2[CH2:15][CH:14]([CH2:17][N:18]3[C:32](=[O:33])[C:25]4[C:26](=[CH:30][CH:31]=[C:23]([N+:20]([O-:22])=[O:21])[CH:24]=4)[C:27]3=[O:28])[O:13][CH2:12][C:11]=2[S:10][C:9]=1[NH2:19])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 691211,2-Benzenedicarboxylic acid, 4-nitro-HCID 81531DiisopropylethylamineHCID 54228347HCID 54228347, compound

Product 1

HCID 69585728HCID 69585728, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a 4-ml scintillating vial, a solution of 2-amino-5-aminomethyl-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester (58 mg, 0.2 mmol) in tetrahydrofuran (2.0 ml) was treated with 4-nitrophthalic acid (63 mg, 0.3 mmol), diisopropylethylamine (190 μl, 1.1 mmol), and 1,3-diisopropylcarbodiimide (120 μl, 0.77 mmol). The reaction mixture was shaken vigorously for 10 seconds before being stirred at 50° C. for 43 hours and at room temperature for 20 h. The solution was diluted with ethyl acetate (25 ml), washed with 0.5N aqueous hydrochloric acid (25 ml), saturated aqueous sodium bicarbonate (25 ml), and brine (25 ml). The organic layer was dried (MgSO4), filtered and the solvent evaporated in vacuo. Crude 2-amino-5-(5-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester was obtained as a solid and used immediately in the next step.

Workup

  1. stirringbefore being stirred at 50° C. for 43 hours and at room temperature for 20 h
  2. washwashed with 0.5N aqueous hydrochloric acid (25 ml), saturated aqueous sodium bicarbonate (25 ml), and brine (25 ml)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-3e141b8ce1b44fed824d2f87b5d02590
Source dataset
uspto-grants-2006_10
Patent number
US07115624B1

Reaction notes

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