HCID 69391299, compound → HCID 69385752, compound

HRID 916806Notes

Reaction equation

[CH3:1][C:2]1(C)[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@H:12]3[O:16]C(=O)[N:14]([CH2:18][CH2:19][C:20]4[CH:44]=[CH:43][C:23]([O:24][CH2:25][CH2:26][O:27][CH2:28][C:29]5[CH:30]=[C:31]([NH:35][C:36]([C:38]6[O:39][CH:40]=[CH:41][CH:42]=6)=[O:37])[CH:32]=[CH:33][CH:34]=5)=[CH:22][CH:21]=4)[CH2:13]3)=[CH:11][C:5]=2[CH2:4][O:3]1.O([Si](C)(C)C)[K]>C1COCC1>[C:2]([OH:7])(=[O:3])[CH3:1].[OH:16][C@H:12]([C:10]1[CH:9]=[CH:8][C:6]([OH:7])=[C:5]([CH2:4][OH:3])[CH:11]=1)[CH2:13][NH:14][CH2:18][CH2:19][C:20]1[CH:44]=[CH:43][C:23]([O:24][CH2:25][CH2:26][O:27][CH2:28][C:29]2[CH:30]=[C:31]([NH:35][C:36]([C:38]3[O:39][CH:40]=[CH:41][CH:42]=3)=[O:37])[CH:32]=[CH:33][CH:34]=2)=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 75 °C

Procedure

N-(3-{[2-(4-{2-[(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]ethyl}phenoxy)ethoxy]methyl}phenyl)-2-furamide (34 mg) in THF (2 mL) was treated with KOSiMe3 (18 mg) and the resulting solution was heated at 75° C. for 4 h. The reaction mixture was then quenched with MeOH and concentrated in vacuo. The residue was then purified by HPLC, before dissolving in acetic acid (1 mL) and water (0.33 mL) and heating at 75° for 20 min. The solution was then concentrated in vacuo and azeotroped with MeOH to give the title compound (3.4 mg). LCMS RT=2.45 min. ES+ve 547 (MH)+

Workup

customThe reaction mixture was then quenched with MeOH
concentrationconcentrated in vacuo
customThe residue was then purified by HPLC
dissolutionbefore dissolving in acetic acid (1 mL)
temperaturewater (0.33 mL) and heating at 75° for 20 min
concentrationThe solution was then concentrated in vacuo
customazeotroped with MeOH

Sources & evidence

ORD record: ord-2e8bfa522a32462f8331652d4b2323c1
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07271197B2

Reaction notes

Loading…