NSC354971 → HCID 86686089, compound

HRID 1520752Notes

Reaction equation

HRID 1520752 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:11](=[O:12])[O:10][C:8](=[O:9])[CH2:7][C:6]2=[CH:13][C:14]=1[O:15][CH3:16].[CH3:17][N:18]=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[NH:26][C:27](=[O:30])[O:28][CH3:29]>C(Cl)(Cl)Cl>[CH3:29][O:28][C:27]([NH:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C@H:19]1[C@@H:7]([C:8]([OH:10])=[O:9])[C:6]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:14]([O:15][CH3:16])[CH:13]=2)[C:11](=[O:12])[N:18]1[CH3:17])=[O:30]

Participants

4

Reactant 2

HCID 337325NSC354971HCID 49856001HCID 49856001, compound

Product 1

HCID 86686089HCID 86686089, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4,5-Dimethoxyhomophthalic anhydride (9, 1.16 g, 5.2 mmol) was added to a solution of 8 (1 g, 5.2 mmol) in chloroform (10 mL) and the mixture was stirred for 2 h at room temperature. The precipitate was filtered, washed with chloroform (2×10 mL) and dried to yield acid cis 10 (750 mg, 35%): mp 212-213° C. (dec). IR (KBr) 1737, 1626, 1599, 1578 cm−1; 1H NMR (300 MHz, methanol-d4) δ 7.80 (s, 1 H), 7.51 (s, 1 H), 7.29 (m, 2 H), 7.11 (t, J=7.0 Hz, 1 H), 6.83 (m, 2 H), 5.33 (d, J=6.60 Hz, 1 H), 4.45 (d, J=6.60 Hz, 1 H), 3.80 (s, 3 H), 3.74 (s, 3 H), 3.65 (s, 3 H), 2.80 (s, 3 H); ESIMS m/z (rel intensity) 851 (35), 459 (13), 436 (100), 415 (6), 215 (15); ESIHRMS m/z MNa+ calcd. for C21H22N2O7, 437.1325; found, 437.1333.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with chloroform (2×10 mL)
  3. customdried

Sources & evidence

ORD record
ord-3d76494c6f524c06991d11008bb53763
Source dataset
uspto-grants-2015_07
Patent number
US09073920B2

Reaction notes

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