Allyl chloroformate → HCID 86718323, compound

HRID 1849936Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

Allyl chloroformate (0.23 mL, 2.2 mmol) was added to a solution of 1 (694 mg, 2 mmol), N,N-diisopropylethylamine (0.7 mL, 4 mmol) in 20 mL MeCN at 0° C. The reaction mixture was stirred at 0° C. for 4 h and concentrated in vacuo. The crude residue was purified by flash column chromatography (2:1→4:1 EtOAc/Hexane) to give 2 (white solid, 65% yield): 1H NMR (400 MHz, DMSO-d6) δ11.05 (s, 1H), 8.19-8.22 (d, 1H), 7.16-7.18 (d, 1H), 6.32-6.37 (t, 1H), 5.93-6.05 (m, 2H), 5.43 (s, 1H), 5.27-5.39 (m, 5H), 4.74-4.75 (d, 2H), 4.67-4.69 (d, 2H), 4.31-4.33 (m, 1H), 3.82-3.84 (m, 1H), 3.73-3.76 (m, 1H).

Workup

concentrationconcentrated in vacuo
customThe crude residue was purified by flash column chromatography (2:1→4:1 EtOAc/Hexane)
customto give 2 (white solid, 65% yield)

Sources & evidence

ORD record: ord-cc2700bb16534117ba047fb343c32911
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08956613B2

Reaction notes

Loading…