Triethylamine → F15845

HRID 1014088Notes

Reaction equation

[O:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][CH2:4][C@H:3]([NH2:12])[CH2:2]1.CC1C=CC(S(O[CH2:24][C@H:25]([CH3:36])[CH2:26][S:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[O:34][CH3:35])(=O)=O)=CC=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:35][O:34][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[S:27][CH2:26][C@@H:25]([CH3:36])[CH2:24][NH:12][C@H:3]1[CH2:4][S:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[O:1][CH2:2]1

Participants

Conditions

Temperature: 105 °C

Procedure

6.5 g (35.9 mmol) of (R)-3,4-dihydro-2H-1,5-benzoxathiepin-3-amine and 11 g (30 mmol) of (S)-3-(2-methoxyphenyl-sulfanyl)-2-methylpropyl 4-methylbenzenesulfonate in 33 ml of toluene are introduced into a three-necked flask under an inert atmosphere. 6 g (60 mmol) of triethylamine are added and then the reaction mixture is heated with stirring at 105° C. for 24 hours. After returning to ambient temperature, 33 ml of toluene are added. The organic phase is washed twice with 66 ml of demineralised water and is then decolourised by stirring for one hour in the presence of 2 g of Black CXV. After concentrating under reduced pressure, driving-off with 33 ml of ethanol 100 is carried out. The title product is obtained in the form of a yellow oil (8.85 g; 79%).

Workup

temperaturethe reaction mixture is heated
customAfter returning to ambient temperature
washThe organic phase is washed twice with 66 ml of demineralised water
stirringby stirring for one hour in the presence of 2 g of Black CXV
concentrationAfter concentrating under reduced pressure, driving-off with 33 ml of ethanol 100

Sources & evidence

ORD record: ord-1b571ddc9f244bbdb4378baa7eeba692
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07982054B2

Reaction notes

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