Tert-Butylamine → HCID 45860617, compound

HRID 1191051Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([OH:13])=O)=[CH:5][CH:4]=1)#[N:2].S(Cl)(Cl)=O.[C:18]([NH2:22])([CH3:21])([CH3:20])[CH3:19].C(N(CC)CC)C>C1(C)C=CC=CC=1.C(Cl)Cl>[C:18]([NH:22][C:11]([CH2:10][CH2:9][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=1)=[O:13])([CH3:21])([CH3:20])[CH3:19]

Participants

Conditions

Temperature: 0 °C

Procedure

Dissolve 3-(4-cyanophenyl)-propionic acid (0.4 g, 2.48 mmol) and thionyl chloride (1.1 mL, 14.9 mmol) in toluene (2 mL) and reflux the mixture for 2 h. Concentrate in vacuo, dissolve the residue in DCM (1.5 mL) and add the solution to a cold solution (0° C.) of tert-butylamine (300 μL, 2.85 mmol) in DCM (1.5 mL) and triethylamine (97 μL, 0.69 mmol). Allow the mixture to stir at 0° C. for 15 min and at room temperature for 16 h. Add water, separate the organic phase and extract the aqueous phase twice with DCM. Dry the combined organic extracts over Na2SO4, filter and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (65:35) to obtain the desired intermediate (306 mg, 54%).

Workup

temperaturereflux the mixture for 2 h
concentrationConcentrate in vacuo
dissolutiondissolve the residue in DCM (1.5 mL)
customAdd water, separate the organic phase
extractionextract the aqueous phase twice with DCM
dry with materialDry the combined organic extracts over Na2SO4
filtrationfilter
concentrationconcentrate in vacuo
customPurify by chromatography on silica gel eluting with hexane/EtOAc (65:35)

Sources & evidence

ORD record: ord-764aefe8bb32489fa68fcbe32c220b07
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680091B2

Reaction notes

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