Potassium Carbonate → (+/-)-cis-2-(4-methoxyphenyl)-3-acetoxy-5-[2-(N-methyl-N-n-propylamino)ethyl]-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one oxalate

HRID 1285354Notes

Reaction equation

HRID 1285354 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:15]([O:16][C:17](=[O:19])[CH3:18])[C:14](=[O:20])[NH:13][C:12]3[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:11]=3[S:10]2)=[CH:5][CH:4]=1.Cl.[CH3:27][N:28]([CH2:32][CH2:33]Cl)[CH2:29][CH2:30][CH3:31].C(=O)([O-])[O-].[K+].[K+].[C:41]([O-:46])(=[O:45])[C:42]([O-:44])=[O:43]>CC(C)=O>[C:41]([OH:46])(=[O:45])[C:42]([OH:44])=[O:43].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[C@@H:15]([O:16][C:17](=[O:19])[CH3:18])[C:14](=[O:20])[N:13]([CH2:33][CH2:32][N:28]([CH3:27])[CH2:29][CH2:30][CH3:31])[C:12]3[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:11]=3[S:10]2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 71081OxalateHCID 30312081-Propanamine, N-(2-chloroethyl)-N-methyl-, hydrochlorideHCID 70453288(+)-cis-2-(4-methoxyphenyl)-3-acetoxy-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

Product 1

HCID 86740629(+/-)-cis-2-(4-methoxyphenyl)-3-acetoxy-5-[2-(N-methyl-N-n-propylamino)ethyl]-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one oxalate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1 g of (±)-cis-2-(4-methoxyphenyl)-3-acetoxy-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, 0.55 g of 2-(N-methyl-N-n-propylamino)ethyl chloride hydrochloride, 0.95 g of potassium carbonate and 20 ml of acetone is treated in the same manner as described in Example 1. The product thus obtained is converted into its oxalate and recrystallized from a mixture of chloroform and ethanol. 1.1 g of (±)-cis-2-(4-methoxyphenyl)-3-acetoxy-5-[2-(N-methyl-N-n-propylamino)ethyl]-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one oxalate are thereby obtained as colorless needles.

Workup

  1. additionis treated in the same manner
  2. customThe product thus obtained
  3. customrecrystallized from a mixture of chloroform and ethanol

Sources & evidence

ORD record
ord-2fbb49e6108e4489a319f5d2c62486c9
Source dataset
uspto-grants-1986_01
Patent number
US04567175

Reaction notes

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