Hydrochloric Acid → 133261-17-3

HRID 2054738Notes

Reaction equation

Br[CH2:2][C:3]([NH:5][C@H:6]([CH3:20])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([S:16]([NH2:19])(=[O:18])=[O:17])[CH:9]=1)=[O:4].CC(C)([O-])C.[K+].[CH2:27]([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[OH:36])[CH3:28].Cl>O1CCCC1.C(OCC)(=O)C>[CH2:27]([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[O:36][CH2:2][C:3]([NH:5][C@H:6]([CH3:20])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([S:16]([NH2:19])(=[O:18])=[O:17])[CH:9]=1)=[O:4])[CH3:28]

Participants

Conditions

Temperature: 25 °C

Procedure

1.0 g of (R)-2-bromo-N-[2-(4-methoxy-3-aminosulfonyl-phenyl)-1-methyl-ethyl]-acetamide prepared in Example 2 was added to a stirring solution of 1.25 g of potassium t-butoxide and 1.5 g of 2-ethoxy phenol in 10 ml of tetrahydrofuran and stirred at 25° C. for 1 hour. After the reaction was completed, 50 ml of a 10% hydrochloric acid solution and then, 50 ml of ethyl acetate was added to the resultant solution and then, extracted. Next, the organic layer was separated and concentrated. 10 ml of methanol was added to the obtained concentrated residue and stirred for 12 hours. Then, the resultant product was filtered and dried to obtain the title compound as a white solid (0.9 g).

Workup

extractionextracted
customNext, the organic layer was separated
concentrationconcentrated
addition10 ml of methanol was added to the obtained concentrated residue
stirringstirred for 12 hours
filtrationThen, the resultant product was filtered
customdried

Sources & evidence

ORD record: ord-825d2446d5274f9f84eab1576c51c4de
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07329780B2

Reaction notes

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