Bromotrichloromethane → HCID 67234103, compound

HRID 2261273Notes

Reaction equation

C(N(S(F)(F)F)CC)C.[CH3:10][O:11][C:12](=[O:28])[CH:13]([NH:16][C:17](=[O:27])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)[CH2:14]O.C(Br)(Cl)(Cl)Cl.C1CCN2C(=NCCC2)CC1.C([O-])(O)=O.[Na+]>ClCCl>[CH3:10][O:11][C:12]([C:13]1[N:16]=[C:17]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[O:27][CH:14]=1)=[O:28]

Participants

Conditions

Temperature: -78 °C

Procedure

DAST (diethylaminosulfur trifluoride) was added to a cold (−78° C.) solution of 3-hydroxy-2-[2-(4-methoxy-phenyl)-acetylamino]-propanoic acid methyl ester (400 mg, 1.5 mmol) in dichloromethane (8 mL). After stirring for 1 h at −78° C., CCl3Br (149 μL, 1.5 mmol) and DBU (226 μL, 1.5 mmol) were added and the reaction was allowed to warm to 25° C. and stirred at this temperature for 12 h. The reaction was poured into saturated aqueous NaHCO3 and the biphasic mixture was extracted with DCM. The combined organic extracts were dried with MgSO4 and purified by column chromatography (hexanes:ethyl acetate from 25 to 100%). 2-(4-Methoxy-benzyl)-oxazole-4-carboxylic acid methyl ester was isolated as a white solid (80 mg, 21%). ESI-MS m/z calc. 247.5, found 248.2 (M+1)+. Retention time of 2.64 minutes. 1H NMR (400 MHz, CDCl3) δ 3.80 (s, 3H), 3.92 (s, 3H), 4.12 (s, 2H), 6.87 (d, J=8.0 Hz, 2H), 7.24 (d, J=8.0 Hz, 2H).

Workup

temperatureto warm to 25° C.
stirringstirred at this temperature for 12 h
extractionthe biphasic mixture was extracted with DCM
dry with materialThe combined organic extracts were dried with MgSO4
custompurified by column chromatography (hexanes:ethyl acetate from 25 to 100%)

Sources & evidence

ORD record: ord-b845fa69d0d742a791edaff00e44da53
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07846951B2

Reaction notes

Loading…