Dimethylformamide → HCID 50915133, compound

HRID 2176428Notes

Reaction equation

O[C:2]1[C:3](O)=[CH:4][C:5]2[CH2:6][C@H:7]3[C:31](=[O:32])[N:30]([CH3:33])[CH2:29][C:28](=[O:34])[N:8]3[C@H:9]([C:12]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14](C(OC(C)(C)C)=O)[CH:13]=3)[C:10]=2[CH:11]=1.[C:36]([O-])([O-:38])=[O:37].[Cs+].[Cs+].CN(C=O)C.BrCCl>CCOC(C)=O>[NH:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12]([C@H:9]2[N:8]3[C@H:7]([C:31](=[O:32])[N:30]([CH3:33])[CH2:29][C:28]3=[O:34])[CH2:6][C:5]3[CH:4]=[C:3]4[O:37][CH2:36][O:38][C:2]4=[CH:11][C:10]2=3)=[CH:13]1

Participants

Conditions

Temperature: 150 °C

Procedure

0.665 g (1.4 mmol) (5) and 0.6853 g (2.1 mmol) Cs2CO3 was suspended in 3.3 ml freshly distilled DMF. 0.140 ml (2.1 mmol) BrCH2Cl was added and the mixture was heated at 150° C. for 1.5 h. The heat source was removed and the mixture was allowed to cool to r.t. after which the mixture was filtered and separated with 100 ml EtOAc and 100 ml H2O. The water phase was extracted with 2×100 ml EtOAc. The pooled organic phases were washed with 150 ml brine, dried over Na2SO4, filtered and evaporated. Flash chromatography (Pet. ether:EtOAc, 1:4) gave 0.167 g (0.43 mmol, 31%) (6).

Workup

customThe heat source was removed
temperatureto cool to r.t. after which the mixture
filtrationwas filtered
customseparated with 100 ml EtOAc and 100 ml H2O
extractionThe water phase was extracted with 2×100 ml EtOAc
washThe pooled organic phases were washed with 150 ml brine
dry with materialdried over Na2SO4
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-60380073513f4d219af53d5ad09d7978
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09066947B2

Reaction notes

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