Methyl chloroformate → HCID 70674229, compound

HRID 1747720Notes

Reaction equation

Cl.Cl.Cl.[F:4][C:5]1[CH:29]=[CH:28][CH:27]=[CH:26][C:6]=1[CH2:7][C:8]1[N:12]2[N:13]=[CH:14][CH:15]=[CH:16][C:11]2=[C:10]([C:17]2[N:22]=[C:21]([NH2:23])[C:20]([NH2:24])=[C:19]([NH2:25])[N:18]=2)[N:9]=1.Cl[C:31]([O:33][CH3:34])=[O:32]>N1C=CC=CC=1>[CH:31]([OH:33])=[O:32].[NH2:25][C:19]1[C:20]([NH:24][C:31](=[O:32])[O:33][CH3:34])=[C:21]([NH2:23])[N:22]=[C:17]([C:10]2[N:9]=[C:8]([CH2:7][C:6]3[CH:26]=[CH:27][CH:28]=[CH:29][C:5]=3[F:4])[N:12]3[C:11]=2[CH:16]=[CH:15][CH:14]=[N:13]3)[N:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1.84 g (4.642 mmol) of the compound prepared in Example 9A were initially charged in pyridine (35 ml), 0.359 ml (4.642 mmol) of methyl chloroformate was added at 0° C. and the mixture was stirred at 0° C. for 10 min. After 16 hours of stirring at 20° C., the reaction mixture was poured into ice-water and extracted three times with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The residue was purified by chromatography on silica gel (mobile phase:gradient dichloromethane:methanol 100:5 to dichloromethane:methanol 2:1). This gave 1.13 g of the target compound (53% of theory).

Workup

stirringAfter 16 hours of stirring at 20° C.
extractionextracted three times with ethyl acetate
washThe combined organic phases were washed with saturated aqueous sodium chloride solution
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified by chromatography on silica gel (mobile phase:gradient dichloromethane:methanol 100:5 to dichloromethane:methanol 2:1)

Sources & evidence

ORD record: ord-13a991ad9ed241ce8e740ebc2793952d
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150580B2

Reaction notes

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