2-Butenoyl chloride → HCID 11223672, compound

HRID 2243834Notes

Reaction equation

[C:1]([N:6]1[C@@:10]2([CH2:14][CH2:13][N:12]([C@@H:15]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])[CH2:16][CH:17]([CH3:19])[CH3:18])[C:11]2=[O:30])[CH2:9][CH2:8][CH2:7]1)(=[O:5])[CH:2]([CH3:4])[CH3:3].CC=CC(Cl)=O>>[CH3:4][C:2](=[CH2:3])[C:1]([N:6]1[C@@:10]2([CH2:14][CH2:13][N:12]([C@@H:15]([C:20]([O:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[O:21])[CH2:16][CH:17]([CH3:19])[CH3:18])[C:11]2=[O:30])[CH2:9][CH2:8][CH2:7]1)=[O:5]

Participants

Reactant 2

HCID 790802-Butenoyl chloride

HCID 11200815HCID 11200815, compound

Product 1

HCID 11223672HCID 11223672, compoundYield 50%

Procedure

Following the procedure described for the synthesis of 13, staffing from 11 (200 mg, 0.43 mmol) and methylacryloyl chloride (89 mg, 0.86 mmol), the title compound (70 mg, 50%) was obtained as a colourless oil, after purification by LC (silica gel, hex-EtOAc, 2:1). HPLC [Column Novapack C18 (Waters), 3.9×150 mm, Φ=1 ml/min, λ=214 nm, eluent: ACN/0.05% TFA, (25/75)] Rt==6.38 min. 1H-NMR (200 MHz, CDCl3) δ 0.91 (t, J=6, 6H), 1.44 (m, 1H), 1.64-1.93 (m, 5H), 1.93 (s, 3H), 1.96-2.12 (m, 2H), 2.78 (m, 1H), 3.20 (m, 1H), 3.56-3.68 (m, 3H), 4.80 and 4.77 (2d, J=10, 1H), 5.16 (s, 2H), 5.19 (d, J=9, 2H), 7.32 (m, 5H). 13C-NMR (75 MHz, CDCl3) δ 19.8, 21.4, 23.0, 24.2, 24.9, 29.9, 37.1, 37.7, 41.1, 50.2, 53.2, 66.6, 67.4, 116.9, 128.1, 128.3, 128.4, 135.0, 141.7, 170.7, 174.1. ESI-MS Calcd for C24H32N2O4: 412.24. Found: 413.3 (M+H)+.

Sources & evidence

ORD record: ord-55afa1320dc3423fa714d5a4efbc8cbe
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07678765B2

Reaction notes

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