HCID 86749353, compound → HCID 86749356, compound

HRID 1440811Notes

Reaction equation

[OH:1][C@H:2]1[C@H:11]([N:12]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:21])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:22]3[C:23](=[O:31])[C:24](=[O:30])[C:25]=3[O:26]C(C)C)[CH:9]=2)[O:4][C:3]1([CH3:33])[CH3:32]>C1COCC1.Cl>[OH:31][C:23]1[C:24](=[O:30])[C:25](=[O:26])[C:22]=1[C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[O:4][C:3]([CH3:33])([CH3:32])[C@@H:2]([OH:1])[C@@H:11]2[N:12]1[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]1=[O:21]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 303 mg (0.676 retool) of 3-[trans-3-hydroxy-2,2-dimethyl-4-(1- oxo-1,3-dihydroisoindol-2-yl)-chroman-6-yl]-4-isopropoxy-cyclobut-3-ene-1,2-dione in THF (5 mL) containing 1.13 mL (6 N HCl) was heated at 50° C. for 48 h. The reaction mixture was diluted with 2 N HCl and extracted into 20% THF-CH2Cl2. The combined organic extracts were dried (MgSO4), concentrated, and recrystallized from THF to give 112 mg of the title compound as a tan solid, mp>250° C.: 1H-NMR (DMSO-d6 ; 400 MHz) δ7.84 (dd, 1 H), 7.81 (d, 1 H), 7.52-7.64 (m, 3 H), 7.51 (s, 1 H), 6.93 (d, 1 H), 5.3 (br s, 1 H), 4.4-4.5 (br d, 1 H), 3.8-4.1 (br, 2 H), 1.47 (s, 3 H), and 1.26 ppm (s, 3 H); IR (KBr) 3400, 1785, 1720, 1670, and 1600 cm-1 ; mass spectrum (DCI+), m/e 406 (M+H). Anal. Calcd. for C23H19NO6. 0.5 H2O: C, 66.66; H, 4.86; N, 3.38 Found: C, 66.67; H, 4.60; N, 3.34.

Workup

extractionextracted into 20% THF-CH2Cl2
dry with materialThe combined organic extracts were dried (MgSO4)
concentrationconcentrated
customrecrystallized from THF

Sources & evidence

ORD record: ord-1e6d69519b0f43679dd2a8ffe7e3836a
Source dataset: uspto-grants-1996_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05500442

Reaction notes

Loading…