Formic Acid → HCID 57779597, compound

HRID 509190Notes

Reaction equation

[CH:1]([OH:3])=O.C(OC(=O)C)(=O)C.[CH:11]([NH:24][OH:25])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>[OH-].[Na+]>[CH:11]([N:24]([OH:25])[CH:1]=[O:3])([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 55 °C

Procedure

Formic acid (0.53 mL, 14.1 mmol) was added dropwise to acetic anhydride (1.07 mL, 11.3 mmol) at 0° C., stirred for 5 mins. and then warmed to 55° C. for 5 mins prior to cooling back down to room temperature. N-benzhydrylhydroxylamine 41 (225 mg, 1.13 mmol) was added, and stirred at room temperature for 3 days. The reaction mixture was diluted with aqueous NaOH solution (to pH=7), the solution was stirred for 5 mins, and then acidified with aqueous HCl solution (to pH=4). Following extraction with ethyl acetate, the combined organic layers were dried with anhydrous sodium sulfate, filtered, and concentrated. The crude material was concentrated and purified by silica gel column chromatography with gradient of ethyl acetate (0-75%) in hexane to afford compound 42 as a tan solid (169 mg, 66%). 1H NMR: (DMSO-d6) 8.41 (br s, 1H), 7.44-7.28 (m, 11H). LRMS (ESI): (calc.) 227.3 (found) 228.2 (MH)+.

Workup

temperatureto cooling back down to room temperature
stirringstirred at room temperature for 3 days
stirringthe solution was stirred for 5 mins
extractionextraction with ethyl acetate
dry with materialthe combined organic layers were dried with anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated
concentrationThe crude material was concentrated
custompurified by silica gel column chromatography with gradient of ethyl acetate (0-75%) in hexane

Sources & evidence

ORD record: ord-9930f601bf8e4b11b1dbf8babe114212
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096565B2

Reaction notes

Loading…