Phthalic Anhydride → HCID 86660588, compound

HRID 718727Notes

Reaction equation

HRID 718727 reaction equation
Cl.[NH2:2][C:3]1([CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:8][CH2:7][C:6](=[O:9])[NH:5][C:4]1=[O:10].[C:26]1(=O)[O:31][C:29](=[O:30])[C:28]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:27]12.C([O-])(=O)C.[Na+]>C(O)(=O)C>[O:30]=[C:29]1[C:28]2[C:27](=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:26](=[O:31])[N:2]1[C:3]1([CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:8][CH2:7][C:6](=[O:9])[NH:5][C:4]1=[O:10]

Participants

5

Reactant 3

HCID 6811Phthalic AnhydrideHCID 517045Sodium AcetateHCID 86660583HCID 86660583, compound

Product 1

HCID 86660588HCID 86660588, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
130 °C

Procedure

To a suspension of 4 (0.12 g, 0.324 mmol), phthalic anhydride (0.060 g, 0.401 mmol), and sodium acetate (0.037 g, 0.434 mmol) was added acetic acid (1.5 mL) and the resulting mixture was stirred at 130° C. After 7 h, the mixture was quenched with sodium bicarbonate and extracted with DCM. The organic layer was dried over MgSO4 and concentrated. Purification by preparative HPLC afforded 12. Rf=0.32 (95:5 DCM:MeOH). 1H NMR (400 MHz, CDCl3) δ 8.05-7.64 (m, 5H), 7.44-7.27 (m, 4H), 5.16-5.00 (m, 2H), 4.90 (m, 1H), 3.34-3.09 (m, 3H), 2.92-2.77 (m, 1H), 2.77-2.45 (m, 3H), 2.36-2.18 (m, 1H), 2.17-1.99 (m, 1H), 1.38 (d, J=6.8 Hz, 2H). MS (ESI) m/z calcd for C25H26N3O6 [M+H]+ 464.5, found 464.3.

Workup

  1. customthe mixture was quenched with sodium bicarbonate
  2. extractionextracted with DCM
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-10fb144f53724b478126c0ed2293c712
Source dataset
uspto-grants-2015_11
Patent number
US09193989B2

Reaction notes

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