Dimethyl Sulfoxide → HCID 86758819, compound

HRID 1057473Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([O:15][C:16]([N:18]([CH2:23][C:24]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=1[Br:31])[CH2:19][CH2:20][CH2:21]O)=[O:17])([CH3:14])([CH3:13])[CH3:12].CCN(C(C)C)C(C)C.C1(P(=[CH:60][C:61]([O:63][CH3:64])=[O:62])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[C:11]([O:15][C:16]([N:18]([CH2:19][CH2:20]/[CH:21]=[CH:60]/[C:61]([O:63][CH3:64])=[O:62])[CH2:23][C:24]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=1[Br:31])=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

Conditions

Temperature: -65 °C

Procedure

Oxalyl chloride (1.8 eq) was added to a stirred solution of dimethylsulfoxide (3.8 eq) in methylene chloride (0.25 M) at −78° C. maintaining the temperature<−65° C. After 20 min, a solution of N-(tert-butoxycarbonyl)-N-((2-bromo-5-fluorophenyl)methyl)-N-(3-hydroxypropyl)amine (1 eq) was added and the resulting mixture stirred 30 minutes. Hunig's base (4 eq) was added and the reaction allowed to warm to RT. The mixture was then cooled to 15° C. and methyl (triphenylphosphoranylidene)acetate was added. The resulting mixture was stirred 12 h and purified by flash chromatography on silica gel (10-20% ethyl acetate/hexane) to give methyl (2E)-5-(N-(tert-butoxycarbonyl)-N-((2-bromo-5-fluorophenyl)methyl) amino)pent-2-enoate as a clear oil. EI-MS m/z 474, 476 (M−H+HOAc)−

Workup

temperatureto warm to RT
temperatureThe mixture was then cooled to 15° C.
stirringThe resulting mixture was stirred 12 h
custompurified by flash chromatography on silica gel (10-20% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-c3cd69363ae84a19b11039fc8949b1d4
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06514964B1

Reaction notes

Loading…