Potassium Carbonate → 1,2,3,3a,7,7a-Hexahydro-4-thia-2-aza-cyclopenta[alpha]pentalene-5-carboxylic acid methyl ester

HRID 30237Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[S:22][C:8]2[CH:9]3[CH:13]([CH2:14][C:7]=2[CH:6]=1)[CH2:12][N:11](CC1C=CC=CC=1)[CH2:10]3)=[O:4].C([O-])([O-])=O.[K+].[K+].CC(Cl)OC(Cl)=O>ClCCCl>[CH3:1][O:2][C:3]([C:5]1[S:22][C:8]2[CH:9]3[CH:13]([CH2:14][C:7]=2[CH:6]=1)[CH2:12][NH:11][CH2:10]3)=[O:4]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of the product from step b) (100 mg, 0.32 mmol) in DCE (1.6 ml) was added powdered K2CO3 (176 mg, 1.28 mmol) and ACE-Cl (183 mg, 1.28 mmol). The reaction mixture was heated to 80° C. and stirred for 18 hours. The reaction was cooled to room temperature, filtered, and concentrated in vacuo. The crude oil was dissolved in anhydrous MeOH (2.5 ml) and stirred at room temperature for 3 hours. The solvent was evaporated and the product triturated with anhydrous ether to give a white solid, which was filtered to give the titled compound as its hydrochloride salt: (42.3 mg, 51%), 1H NMR (300 MHz, DMSO, ppm) 2.68 (br d, J=16 Hz, 1H), 2.98-3.06 (m, 2H), 3.19-3.28 (m, 1H), 3.35-3.50 (m, 2H), 3.52-3.62 (m, 1H), 3.80 (s, 3H), 4.00-4.11 (m, 1H), 7.56 (s, 1H), 9.05 (br s, 1H), 9.31 (br s, 1H). MS calculated for C11H13NO2S+H 224, observed 224.

Workup

temperatureThe reaction was cooled to room temperature
filtrationfiltered
concentrationconcentrated in vacuo
dissolutionThe crude oil was dissolved in anhydrous MeOH (2.5 ml)
stirringstirred at room temperature for 3 hours
customThe solvent was evaporated
customthe product triturated with anhydrous ether
customto give a white solid, which
filtrationwas filtered

Sources & evidence

ORD record: ord-c2356eab904a48a39d1543985db7713a
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07423056B2

Reaction notes

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