Potassium Carbonate → HCID 70050987, compound

HRID 1683157Notes

Reaction equation

HRID 1683157 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@@H:14]([OH:15])[C:13](=[O:16])[NH:12][C:11]3[CH:17]=[CH:18][C:19]([CH2:21][O:22][C:23]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:20][C:10]=3[S:9]2)=[CH:4][CH:3]=1.Cl.[CH3:43][N:44]([CH3:48])[CH2:45][CH2:46]Cl.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[C@@H:14]([OH:15])[C:13](=[O:16])[N:12]([CH2:46][CH2:45][N:44]([CH3:48])[CH3:43])[C:11]3[CH:17]=[CH:18][C:19]([CH2:21][O:22][C:23]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[CH:20][C:10]=3[S:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 70050914HCID 70050914, compound

Product 1

HCID 70050987HCID 70050987, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture comprising 2.48 g of (-)-cis-2-(4-methylphenyl)-3-hydroxy-8-trityloxymethyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, 0.75 g of 2-(dimethylamino)ethyl chloride hydrochloride, 1.70 g of potassium carbonate and 50 ml of acetone was refluxed overnight while stirring. After the mixture was cooled, insoluble materials were removed by filtration, and the filtrate was concentrated under reduced pressure. The residual was recrystallized from a mixed solution of ethyl acetate and n-hexane to give 2.59 g of (-)-cis-2-(4-methylphenyl)-3-hydroxy-5-[2-(dimethylamino)ethyl]-8-trityloxymethyl-2,3-dihydro-1,5-benzothiazepin-4(5H) -one.

Workup

  1. temperaturewas refluxed overnight
  2. temperatureAfter the mixture was cooled
  3. custominsoluble materials were removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residual was recrystallized from a mixed solution of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-6571b48426b14c1ca12f56defe42bd19
Source dataset
uspto-grants-1997_06
Patent number
US05637582

Reaction notes

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