Dicyclohexylcarbodiimide → HCID 70381223, compound

HRID 1247983Notes

Reaction equation

HRID 1247983 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:15]([OH:16])[C:14](=[O:17])[N:13]([CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])[C:12]3[CH:23]=[CH:24][CH:25]=[CH:26][C:11]=3[S:10]2)=[CH:5][CH:4]=1.[CH3:27][O:28][C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][C:37]=1[N+:38]([O-:40])=[O:39])[C:32](O)=[O:33].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C)C=O.CN(C)C1C=CN=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[C@@H:15]([O:16][C:32](=[O:33])[C:31]3[CH:35]=[CH:36][C:37]([N+:38]([O-:40])=[O:39])=[C:29]([O:28][CH3:27])[CH:30]=3)[C:14](=[O:17])[N:13]([CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])[C:12]3[CH:23]=[CH:24][CH:25]=[CH:26][C:11]=3[S:10]2)=[CH:7][CH:8]=1

Participants

7

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 787643-Methoxy-4-nitrobenzoic acidHCID 91638Deacetyldiltiazem

Product 1

HCID 70381223HCID 70381223, compoundYield 67.5%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

1.2 g of (+)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(dimethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, 1.08 g of 3-methoxy-4-nitrobenzoic acid and 0.96 g of dicyclohexylcarbodiimide are dissolved in a mixture of 30 ml of methylene chloride and 8 ml of dimethylformamide under ice-cooling. A catalytic amount of 4-(dimethylamino)pyridine is added to the solution, and said mixture is stirred at room temperature overnight. After the reaction, the precipitates are removed by filtration. The filtrate is washed with an aqueous potassium carbonate solution and then with water, dried and evaporated to remove solvent. The residue is purified by silica gel chromatography (solvent, chloroform:methanol=20:0.3). 1.2 g of (+)-cis-2-(4-methoxyphenyl)-3-(3-methoxy-4-nitrobenzoyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one are thereby obtained as an oil. Yield: 67.4%.

Workup

  1. temperaturecooling
  2. customAfter the reaction
  3. customthe precipitates are removed by filtration
  4. washThe filtrate is washed with an aqueous potassium carbonate solution
  5. dry with materialwith water, dried
  6. customevaporated
  7. customto remove solvent
  8. customThe residue is purified by silica gel chromatography (solvent, chloroform:methanol=20:0.3)

Sources & evidence

ORD record
ord-ecdb0227217042d08e77e131f59df1f5
Source dataset
uspto-grants-1985_06
Patent number
US04521430

Reaction notes

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