Cyanuric chloride → HCID 69515850, compound

HRID 1297239Notes

Reaction equation

[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][C:9]1([C:15](=O)[NH2:16])[CH2:11][CH:10]1[CH:12]([CH3:14])[CH3:13])([CH3:4])([CH3:3])[CH3:2].N1C(Cl)=NC(Cl)=NC=1Cl.[OH-].[Na+]>CN(C=O)C>[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][C:9]1([C:15]#[N:16])[CH2:11][CH:10]1[CH:12]([CH3:13])[CH3:14])([CH3:2])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (1-carbamoyl-2-isopropyl-cyclopropylmethyl)-carbamic acid tert-butyl ester (6.4 g, 24.9 mmol) in dry DMF (100 mL) was added cyanuric chloride (6.4 g, 34.9 mmol). The reaction mixture was stirred at 0° C. for 30 minutes and was poured into cold 0.5N NaOH (200 mL). The aqueous phase was extracted with EtOAc (2×150 mL) and the combined organic layer was washed with water and brine and dried over Na2SO4. Removal of excess of solvent, followed by purification of the residue by flash column chromatography using hexanes/EtOAc (9:1) as eluent gave 4.4 g (74%) of (1-cyano-2-isopropyl-cyclopropylmethyl)-carbamic acid tert-butyl ester as a colorless foam: 1H NMR (300 MHz, CDCl3) δ 0.87 (m, 1H), 1.05 (s, 6H), 1.23-1.33 (m, 3H), 1.45 (s, 9H), 3.29 (dd, J=6.3, 14.5 Hz, 1H), 3.47 (dd, J=6.1, 14.6 Hz, 1H), 5.31 (m, 1H); 13C NMR (75 MHz, CDCl3) δ 14.6, 16.9, 21.0, 21.3, 27.1, 33.3, 39.3, 78.5, 122.0, 154.6; MS (APCI) m/z 239 [M+H]+.

Workup

extractionThe aqueous phase was extracted with EtOAc (2×150 mL)
washthe combined organic layer was washed with water and brine
dry with materialdried over Na2SO4
customRemoval of excess of solvent
customfollowed by purification of the residue by flash column chromatography

Sources & evidence

ORD record: ord-cc079005c7934491ac09f825286dad18
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07250433B2

Reaction notes

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