Dimethylformamide → HCID 50915133, compound

HRID 405950Notes

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-ab2ce83c82a34fa3b99a3f840a3c013b
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754086B2

Reaction notes

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