Cyanuric chloride → HCID 23589348, compound

HRID 1609824Notes

Reaction equation

[CH2:1]([O:8][CH2:9][CH:10]([NH:14][C:15]([CH:17]([O:22][C:23]([N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)=[O:24])[CH2:18][CH:19]([CH3:21])[CH3:20])=[O:16])[C:11](=O)[NH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C(Cl)=NC(Cl)=NC=1Cl>CN(C=O)C>[CH2:1]([O:8][CH2:9][CH:10]([NH:14][C:15]([CH:17]([O:22][C:23]([N:25]1[CH2:26][CH2:27][O:28][CH2:29][CH2:30]1)=[O:24])[CH2:18][CH:19]([CH3:21])[CH3:20])=[O:16])[C:11]#[N:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Morpholine-4-carboxylic acid 1-(2-benzyloxy-1-carbamoyl-ethylcarbamoyl)-3-methyl-butyl ester (0.100 g, 0.23 mmol) was dissolved in 3 mL of DMF and cooled to 0° C. with an ice-water bath. To this solution was added cyanuric chloride (0.044 g, 0.23 mmol) and the reaction mixture was stirred for 1 h. The reaction was quenched with cold water (2 mL), extracted with EtOAc (3×100 mL), and the organic layers were combined and washed with 100 mL brine. The organic layer was dried over MgSO4, filtered and concentrated to give the crude residue. The residue was purified by chromatography (SiO2, 50% hexane in EtOAc) to give the title compound as a clear oil (0.055 g, 60%); 1H NMR (CDCl3) 7.35 (5H, m), 6.76 (1H, d), 5.1 (2H, m), 4.65 (2H, m), 3.82-3.35 (10H, m), 1.7 (3H, m), 0.95 (6H, m). MS: m/z=404 M+1.

Workup

customThe reaction was quenched with cold water (2 mL)
extractionextracted with EtOAc (3×100 mL)
washwashed with 100 mL brine
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated
customto give the crude residue
customThe residue was purified by chromatography (SiO2, 50% hexane in EtOAc)

Sources & evidence

ORD record: ord-f3c4d4d010ad4f9097fa603b03ebddf0
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06982263B2

Reaction notes

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