Phosgene → HCID 86677888, compound

HRID 1499963Notes

Reaction equation

[C:1]([C:4]1[C:5]([O:23][CH2:24][CH3:25])=[C:6]([CH:12]([NH:15][C:16](=[O:22])[O:17][C:18](C)(C)C)CO)[C:7]([F:11])=[C:8]([Cl:10])[CH:9]=1)(=[O:3])[CH3:2].C(Cl)(Cl)=O>ClCCCl.C1(C)C=CC=CC=1>[C:1]([C:4]1[C:5]([O:23][CH2:24][CH3:25])=[C:6]([CH:12]2[CH2:18][O:17][C:16](=[O:22])[NH:15]2)[C:7]([F:11])=[C:8]([Cl:10])[CH:9]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

tert-Butyl [1-(3-acetyl-5-chloro-2-ethoxy-6-fluorophenyl)-2-hydroxyethyl]carbamate (234 mg, 0.62 mmol) (from Step 8) was dissolved in 1,2-dichloroethane (12 mL) and a solution of 2.0 M phosgene in toluene (0.93 mL) was added. The mixture was heated to 80° C. for 1.5 hours. Evaporation and purification on silica gel using ethyl acetate in hexanes (0-85%) gave the desired compound, 175 mg, 93%. LCMS calculated for C13H14ClFNO4 (M+H)+: m/z=302.1; found: 302.1.

Workup

customEvaporation and purification on silica gel

Sources & evidence

ORD record: ord-8d849acbfd0e410b9c9e3a0e9cb0c896
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199982B2

Reaction notes

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