2,2,2-Trichloroethyl chloroformate → HCID 86691454, compound

HRID 1618857Notes

Reaction equation

[CH3:1][N:2](C)[CH:3]([CH3:22])[CH2:4][C:5]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:6]#[N:7].Cl[C:25]([O:27][CH2:28][C:29]([Cl:32])([Cl:31])[Cl:30])=[O:26]>C1(C)C=CC=CC=1>[C:6]([C:5]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:4][CH:3]([N:2]([CH3:1])[C:25](=[O:26])[O:27][CH2:28][C:29]([Cl:32])([Cl:31])[Cl:30])[CH3:22])#[N:7]

Participants

Conditions

Temperature: 25 °C

Procedure

The product of Step 2 (38 g) was dissolved in toluene (400 mL). To this, 2,2,2-trichloroethyl chloroformate (90 mL) was added. The reaction mixture was heated to reflux under Argon purging for 3 hr. The reaction mixture was allowed to cool to 25° C. and concentrated under vacuum to give ˜200 g crude material. Purification was performed as follows on the BIOTAGE® AB ISOLERA™ flash chromatography system. Crude product (50 g) was loaded on a SNAP cartridge containing 340 g silica gel and eluted using a gradient of acetone and hexane. Fractions containing product were pooled and evaporated under vacuum. Yield of purified product (combined runs): 42 g. 1H NMR (CDCl3): 1.2 δ (3H, —CH—CH3 of isopropyl), 2.8 δ (6H, —N—(CH3)), 2.5, 2.6, 3.1 δ (1H, 1H, 1H —CH2-CH—CH3 of isopropyl), 3.8 δ (3H, —OCH3), 6.8-7.5 δ (9H, phenyl rings). Mass spectrometry: m/z=469 (M+H), 486 (M+H2O)

Workup

temperatureThe reaction mixture was heated
temperatureto reflux under Argon purging for 3 hr
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-74b51f671e56436eb4b43d3f3cdf2f52
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08771964B2

Reaction notes

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