Acetone → HCID 131733809, compound

HRID 708488Notes

Reaction equation

[C:1]([N:9]=[C:10]=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:12]([O:16][C:17](=[O:23])[NH:18][CH2:19][CH2:20][CH2:21][NH2:22])([CH3:15])(C)C.[CH3:24][C:25](C)=O>>[C:1]([NH:9][C:10](=[S:11])[NH:22][CH2:21][CH2:20][CH2:19][NH:18][C:17](=[O:23])[O:16][CH2:12][CH2:15][CH2:24][CH3:25])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 180Acetone

HCID 68284Benzoyl isothiocyanate

HCID 2735700tert-Butyl (3-aminopropyl)carbamate

Product 1

HCID 131733809HCID 131733809, compoundYield 43%

Conditions

Temperature: 60 °C

Procedure

Prepared according to the procedure described by Jubian at al. Angew. Chem, 1995, 107, 1343 and Rasmussen et al. Synthesis, 1988, 456. To a solution of benzoyl isothiocyanate (0.93 g, 5.70 mmol) in acetone (10 mL) was added tert-butyl(3-aminopropyl)carbamate (0.95 g, 5.45 mmol). After heating at 60° C. for 2.5 h, the reaction mixture was concentrated in vacuo. The crude residue was purified via silica gel chromatography (EtOAc-heptane, 0-40%), affording the title compound (0.83 g, 43%). LCMS: Rt=0.93 min, m/z=338.0 (M+1) Method 2m_acidic.

Workup

customPrepared
customChem, 1995, 107, 1343 and Rasmussen et al. Synthesis, 1988, 456
concentrationthe reaction mixture was concentrated in vacuo
customThe crude residue was purified via silica gel chromatography (EtOAc-heptane, 0-40%)

Sources & evidence

ORD record: ord-4c9285d7b0f94f35b8c04592a86ec58d
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174978B2

Reaction notes

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