Potassium Carbonate → Ethyl 4-[4-(ethylmethanesulfonylamino)-2,2-dimethylchroman-6-yloxy]-butyrate

HRID 567062Notes

Reaction equation

[CH3:1][C:2]1([CH3:20])[CH2:11][CH:10]([N:12]([CH2:17][CH3:18])[S:13]([CH3:16])(=[O:15])=[O:14])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:19])[CH:8]=2)[O:3]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32]>CC(N(C)C)=O>[CH2:17]([N:12]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:19][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:8]=2)[O:3][C:2]([CH3:1])([CH3:20])[CH2:11]1)[CH3:18]

Participants

Conditions

Temperature: 115 °C

Procedure

1.0 g (3.3 mmol) of N-[2,2-dimethyl-6-hydroxychroman-4-yl]-N-ethyl-methanesulfonamide (Example 1g) was stirred at 80-90° C. for 30 min with 0.455 g of powdered potassium carbonate in 50 ml of DMA. 0.71 g (0.55 ml, 3.6 mmol) of ethyl 4-bromobutyrate was then added at 60° C. and the mixture was stirred at 115° C. for 90 min. It was then concentrated in vac., the residue was treated with water and aqueous hydrochloric acid, the mixture was taken up in EA, the solution was dried and concentrated, and the residue was chromatographed on silica gel using n-heptane/EA (3:1). Appropriate fractions were crystallized using petroleum ether, 0.74 g, m.p. 40-42° C.

Workup

concentrationIt was then concentrated in vac
addition, the residue was treated with water and aqueous hydrochloric acid
customthe solution was dried
concentrationconcentrated
customthe residue was chromatographed on silica gel
customAppropriate fractions were crystallized

Sources & evidence

ORD record: ord-d342fa1d3f76429da46e29d6aee55011
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06177449B1

Reaction notes

Loading…