Cyclobutanecarbonyl chloride → HCID 20598112, compound

HRID 1839233Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:12][N:13]3[CH2:18][CH2:17][CH2:16][CH:15]([CH2:19][NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:14]3)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH:27]1([C:31](Cl)=[O:32])[CH2:30][CH2:29][CH2:28]1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH2:12][N:13]3[CH2:18][CH2:17][CH2:16][CH:15]([CH2:19][N:20]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[C:31]([CH:27]4[CH2:30][CH2:29][CH2:28]4)=[O:32])[CH2:14]3)[CH2:9][CH2:10][CH2:11]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 203 (0.276 mmol, 102 mg) in CH2Cl2 (2 mL) at 0° C. was treated with cyclobutanecarbonyl chloride (1.5 equiv, 0.414 mmol, 50 μL) and diisopropylethylamine (1.5 equiv, 0.414 mmol, 72 μL) under Ar. After warming to 25° C. and stirring for 12 h, the reaction mixture was purified directly by chromatography (PTLC, SiO2, 20 cm×20 cm, 1 mm, 8:1 hexane-acetone) which provided 204 (100 mg, 124 mg theoretical, 81%) as a yellow oil: Rf 0.27 (SiO2, 8:1 hexane-acetone); LRMS m/z 451 (M+, C28H35ClN2O, requires 451).

Workup

customthe reaction mixture was purified directly by chromatography (PTLC, SiO2, 20 cm×20 cm, 1 mm, 8:1 hexane-acetone) which

Sources & evidence

ORD record: ord-2ed1d1c63f4f48939bfff8d9f7a6a677
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06677332B1

Reaction notes

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