Dimethylformamide → Cis(+)-3-acetyloxy-2,3-dihydro-5-(2-methyl-3-dimethylaminopropyl)-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one oxalate

HRID 1898867Notes

Reaction equation

[C:1]([O:4][C@H:5]1[C:11](=[O:12])[NH:10][C:9]2[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=2[S:7][C@H:6]1[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)(=[O:3])[CH3:2].[OH-:25].[K+].Br[CH2:28][CH:29]([CH3:32])[CH2:30]Cl.[CH3:33][N:34](C)[CH:35]=[O:36]>[NH4+].[Cl-]>[C:35]([OH:36])(=[O:25])[C:1]([OH:4])=[O:3].[C:1]([O:4][C@H:5]1[C:11](=[O:12])[N:10]([CH2:28][CH:29]([CH3:32])[CH2:30][N:34]([CH3:35])[CH3:33])[C:9]2[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=2[S:7][C@H:6]1[C:17]1[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: -7 °C

Procedure

5 g cis(+)-3-acetyloxy-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one were dissolved in 30 ml dimethylformamide, cooled at -7° C. 1.4 g 88% KOH and, after 10 minutes, 3.8 g 1-bromo-3-chloro-2-methylpropane were slowly added. The temperature was then raised to 0° C. and the mixture was stirred for 4 hours. The reaction mixture was then poured in 250 ml 0.6N NH4Cl solution and extracted with CH2Cl2. The collected organic phases were washed with H2O, dried on Na2SO4 and evaporated under reduced pressure. 6.4 g a thick orange oil were obtained and were dissolved in hot isopropyl alcohol. A crystalline solid precipitated by cooling, m.p. 100°-103° C.

Workup

temperatureThe temperature was then raised to 0° C.
extractionextracted with CH2Cl2
washThe collected organic phases were washed with H2O
customdried on Na2SO4
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-31a6cb7d33ac478aa99f33ea1dc5e737
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05571807

Reaction notes

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