Bromotrichloromethane → HCID 67234103, compound

HRID 2217321Notes

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 12h. 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) δ3.80 (s, 3H), 3.92 (s, 3H), 4.12 (s, 2H), 6.87 (d, J=8.0 Hz, 2H).

Workup

temperatureto warm to 25° C.
stirringstirred at this temperature for 12h
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-f2b898158ef642cc97189f5982bd392e
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07407976B2

Reaction notes

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