Butyryl chloride → (+/-)-cis 1-Hydroxy-6-methoxy-3,3,14-trimethyl-7-oxo-2,3,7,14-tetrahydro-1H-benzo[b]chromeno[6,5-g][1,8]naphthyridin-2-yl butyrate

HRID 18041Notes

Reaction equation

HRID 18041 reaction equation
[C:1](Cl)(=[O:5])[CH2:2][CH2:3][CH3:4].[OH:7][C@@H:8]1[C:25]2[C:24]3[N:23]([CH3:26])[C:22]4[N:21]=[C:20]5[CH:27]=[CH:28][CH:29]=[CH:30][C:19]5=[CH:18][C:17]=4[C:16](=[O:31])[C:15]=3[C:14]([O:32][CH3:33])=[CH:13][C:12]=2[O:11][C:10]([CH3:35])([CH3:34])[C@@H:9]1[OH:36]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:1]([O:36][C@@H:9]1[C@H:8]([OH:7])[C:25]2[C:24]3[N:23]([CH3:26])[C:22]4[N:21]=[C:20]5[CH:27]=[CH:28][CH:29]=[CH:30][C:19]5=[CH:18][C:17]=4[C:16](=[O:31])[C:15]=3[C:14]([O:32][CH3:33])=[CH:13][C:12]=2[O:11][C:10]1([CH3:34])[CH3:35])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 8855Butyryl chloride2×HCID 11327222(+/-)-cis-1,2-Dihydroxy-6-methoxy-3,3,14-trimethyl-1,2,3,14-tetrahydro-7h-benzo[b]chromeno[6,5-g][1,8]naphthyridin-7-one

Product 1

HCID 131728189(+/-)-cis 1-Hydroxy-6-methoxy-3,3,14-trimethyl-7-oxo-2,3,7,14-tetrahydro-1H-benzo[b]chromeno[6,5-g][1,8]naphthyridin-2-yl butyrate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

Add 2 equivalents of butyryl chloride to a solution of 0.74 mmol of the compound of Example 3 in 7 ml of anhydrous pyridine in the presence of 4-dimethylaminopyridine. Stir at ambient temperature for 72 hours and then add 5 equivalents of butyryl chloride and stir again for 72 hours and then evaporate to dryness. Chromatography on silica gel allows the expected product to be isolated.

Workup

  1. stirringstir again for 72 hours
  2. customevaporate to dryness
  3. customto be isolated

Sources & evidence

ORD record
ord-09a4b8c957f247f2a2cb894d7487383f
Source dataset
uspto-grants-2010_06
Patent number
US07741325B2

Reaction notes

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