Ethyl orthoformate → HCID 24994043, compound

HRID 1673241Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([NH:10][OH:11])=[NH:9])[CH:5]=[CH:4][C:3]=1[C:12]1[N:17]=[C:16]2[O:18][C:19]([CH3:30])([CH3:29])[CH2:20][CH:21]([NH:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[C:15]2=[CH:14][C:13]=1[C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=1.[CH:38](OCC)(OCC)OCC>B(F)(F)F.CCOCC.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[N:9]=[CH:38][O:11][N:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]1[N:17]=[C:16]2[O:18][C:19]([CH3:29])([CH3:30])[CH2:20][CH:21]([NH:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:25])[CH3:26])[C:15]2=[CH:14][C:13]=1[C:31]1[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a suspension of the product of Step A (61 mg, 0.11 mmol) in 5.0 mL of triethyl orthoformate was added one drop of BF3.Et2O. After stirring at 110° C. for 1 h, the reaction mixture was diluted with EtOAc (20 mL) and washed with saturated aq NaHCO3 (2×50 mL) and brine (50 mL). The organic layer was separated, dried over MgSO4, and concentrated. Chromatography on a Biotage 40+S cartridge using 7:13 v/v EtOAc/hexanes as the eluant afforded the title compound: 1H NMR δ 1.27 (s, 9H), 1.48 (s, 3H), 1.56 (s, 3H), 1.84 (t, J=11.4, 1H), 2.27 (dd, J=6.2, 13.0, 1H), 5.50 (m, 1H), 5.84 (br. s, 1H), 7.01 (d, J=8.3, 2H), 7.16 (d, J=8.2, 2H), 7.45 (m, 1H), 7.58 (s, 1H), 7.96-8.04 (m, 2H), 8.77 (s, 1H).

Workup

washwashed with saturated aq NaHCO3 (2×50 mL) and brine (50 mL)
customThe organic layer was separated
dry with materialdried over MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-5bc079fa34e34ca998b4430697df5a78
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07999107B2

Reaction notes

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