Trifluoroacetic acid → HCID 12041753, compound

HRID 1263632Notes

Reaction equation

HRID 1263632 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([NH2:17])[C:10]([NH2:16])=[CH:11][CH:12]=2)[O:7]1)=[O:5])[CH3:2].[F:18][C:19]([F:24])([F:23])[C:20](O)=O>C(OCC)(=O)C>[CH2:1]([O:3][C:4]([CH:6]1[O:7][C:8]2[C:13](=[CH:12][CH:11]=[C:10]3[NH:16][C:20]([C:19]([F:24])([F:23])[F:18])=[N:17][C:9]3=2)[CH2:14][CH2:15]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 12041752HCID 12041752, compound

Product 1

HCID 12041753HCID 12041753, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl-7,8-diamino-chroman-2-carboxylate (927 mg, 3 mmol) in trifluoroacetic acid (20 mL) was heated to reflux for 6 hours and then concentrated in vacuo to give a residue. The residue was dissolved in ethyl acetate (100 mL) and then washed with saturated NaHCO3 solution (30 mL) and water (2×30 mL), dried over anhydrous Na2SO4. Purification by flash chromatography (30% CH2Cl2-hexanes) afforded 612 mg (65% yield) of the title compound as white solid: mp 134° C.; 1H NMR (400 MHz, CDCl3):[tautamer a]: δ:1.19 (t, J=7.1, 3H), 2.22 (m, 2H), 2.40 (m, 1H), 2.70 (m, 1H), 4.15 (q, J=7 Hz, 2H), 5.14 (m, 1H), 7.02 (d, J=8.0 Hz, 1H), 7.25 (d, J=8.0 Hz, 1H), 14.09 (bs, 1H). [tautamer b]: δ1.19 (t, J=7.1, 3H), 2.22 (m, 2H), 2.40 (m, 1H), 2.70 (m, 1H), 4.15 (q, J=7 Hz, 2H), 5.03 (m, 1H), 7.07 (s, 2H), 13.77 (bs, 1H); IR 3450, 3250, 2980, 2600, 1730, 1600, 1500, 1230 cm−1.

Workup

  1. temperatureto reflux for 6 hours
  2. concentrationconcentrated in vacuo
  3. customto give a residue
  4. washwashed with saturated NaHCO3 solution (30 mL) and water (2×30 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. customPurification by flash chromatography (30% CH2Cl2-hexanes)

Sources & evidence

ORD record
ord-a1ec8842375c4f868ecdd42b6bba721a
Source dataset
uspto-grants-2003_04
Patent number
US06541502B1

Reaction notes

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