Hydrochloric Acid → HCID 21469712, compound

A solution of 3-trimethylsilylbenzoic acid in methylene chloride (12 ml) was cooled to -22° C. and N-methylmorpholine (2.0 ml) was added. To the mixture isobutylchloroformate (0.88 ml) was added. The mixture was stirred for 25 min. followed by the addition of N,O-dimethylhydroxylamine hydrochloride (0.9 g). The mixture was stirred at -22° C. for 1 hr., allowed to warm to room temperature and stirred for 1.5 hr. The reaction mixture was poured into dil HCl and the aqueous phase was extracted with diethyl ether (2×100 ml). The combined organic extracts were washed with dil NaHCO3 and dried over Na2 SO4. The solvent was removed in vacuo and the crude product purified by flash chromatography (10% EtOAc in hexane) to yield 600 mg of the desired product. HRMS calc. 238.1263. Found: 238.1268.

1. stirringThe mixture was stirred at -22° C. for 1 hr
2. stirringstirred for 1.5 hr
3. extractionthe aqueous phase was extracted with diethyl ether (2×100 ml)
4. washThe combined organic extracts were washed with dil NaHCO3
5. customdried over Na2 SO4
6. customThe solvent was removed in vacuo
7. customthe crude product purified by flash chromatography (10% EtOAc in hexane)

ORD record

ord-46c3888bcd1d448d9e3011a5da1a8d4c

Source dataset

uspto-grants-1997_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05693668