Potassium Carbonate → HCID 43186137, compound

HRID 2409375Notes

Reaction equation

Br[CH:2]1[CH2:6][CH2:5][O:4][C:3]1=[O:7].C([NH:15][CH2:16][CH2:17][SH:18])(OC(C)(C)C)=O.C([O-])([O-])=O.[K+].[K+].Cl.CCOC(C)=O>CC#N.CCOC(C)=O>[NH2:15][CH2:16][CH2:17][S:18][CH:2]1[CH2:6][CH2:5][O:4][C:3]1=[O:7]

Participants

Conditions

Temperature: 80 °C

Procedure

3-Bromo-dihydro-furan-2-one (2.49 g, 15.1 mmol) and 2-(Boc-amino)ethanethiol (2.9 g, 16.5 mmol) were dissolved in 40 mL of CH3CN. Then K2CO3(4.14 g, 30 mmol) was added to the solution. Let it stir at 80° C. for 16 h. The solvent was evaporated to dryness and the residue was purified by column chromatography (PE/EtOAc=4/1) to 3.8 g of BOC protected Intermediate 29 as colorless oil. The previous compound (3.7 g, 14.16 mmol) was dissolved in 10 ml of EtOAc. Then 40 mL of 4N HCl/EtOAc was added to the solution. Let it stir at 25° C. for 2 h. The white solid was filtered and washed with PE to give 2 g of Intermediate 29.

Workup

customThe solvent was evaporated to dryness
customthe residue was purified by column chromatography (PE/EtOAc=4/1) to 3.8 g of BOC protected Intermediate 29 as colorless oil
stirringstir at 25° C. for 2 h
filtrationThe white solid was filtered
washwashed with PE

Sources & evidence

ORD record: ord-3cdf82e3e2044b68bef200c34841ed13
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815873B2

Reaction notes

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