Sodium Hydroxide → HCID 21057794, compound

HRID 1374030Notes

Reaction equation

[NH:1]1[CH2:7][CH2:6][CH2:5][C@H:2]1[CH2:3][OH:4].[OH-].[Na+].Cl[C:11]1[N:16]=[C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([Cl:26])[CH:19]=2)[N:14]=[C:13]([NH:27][CH:28]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)[N:12]=1>C1C=CC=CC=1>[Cl:26][C:20]1[CH:19]=[C:18]([NH:17][C:15]2[N:14]=[C:13]([NH:27][CH:28]3[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]3)[N:12]=[C:11]([O:4][CH2:3][CH:2]3[CH2:5][CH2:6][CH2:7][NH:1]3)[N:16]=2)[CH:23]=[CH:22][C:21]=1[O:24][CH3:25]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of prolinol (0.0243 g, 2.27 mmol) and sodium hydroxide (95 mg, 2.27 mmol) in benzene (10 mL) was heated to reflux for 2 hours with stirring under nitrogen atmosphere and then cooled to 25° C. followed by the addition of compound 133 (0.3 g, 0.78 mmol) at same temperature. The mixture was heated to reflux for 6 hours, concentrated under vacuum and diluted with water (10 mL). The precipitated solid was filtered off and purified by column chromatography (1–2% MeOH—CHCl3) to afford the title compound E22 as an off-white solid (0.35 g, quantitative). mp 84–86° C.; HPLC: Inertsil ODS 3V (250×4.6 mm) 5 microns [solvent A=0.01 M KH2PO4 (pH 7.0); solvent B=CH3CN], Gradient elution program: T/% B=0/60, 10/60, 25/80, 40/80, 45/60, 50/60; 268 nm, Rt 24.67 min, 99.59% purity; MS (CI): m/z 447 (M+H, 100).

Workup

temperaturewas heated
temperatureto reflux for 2 hours
temperatureThe mixture was heated
temperatureto reflux for 6 hours
concentrationconcentrated under vacuum
additiondiluted with water (10 mL)
filtrationThe precipitated solid was filtered off
custompurified by column chromatography (1–2% MeOH—CHCl3)

Sources & evidence

ORD record: ord-0fc68b4bccfd4d21a1367da8c2e05e0e
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07163943B2

Reaction notes

Loading…