Sodium Iodide → N-[(5S)-3-(4-{4-methylpiperazin-1-ylmethyl}phenylcarbonyloxy)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl]acetamide

HRID 720945Notes

Reaction equation

HRID 720945 reaction equation
C(OC(N[C@H](CCCCNC(OC(C)(C)C)=O)C(NCC[C:15]([O:17][C:18]1[CH:19]=[CH:20][C:21]2[C:27]3[C:28]([O:36][CH3:37])=[C:29]([O:34][CH3:35])[C:30]([O:32][CH3:33])=[CH:31][C:26]=3[CH2:25][CH2:24][C@H:23]([NH:38][C:39](=[O:41])[CH3:40])[C:22]=2[CH:42]=1)=[O:16])=O)=O)(C)(C)C.[CH3:55][N:56]1[CH2:61][CH2:60][NH:59][CH2:58][CH2:57]1.[I-].[Na+]>C(#N)C>[CH3:55][N:56]1[CH2:61][CH2:60][N:59]([CH2:27][C:21]2[CH:22]=[CH:42][C:18]([C:15]([O:17][C:18]3[CH:19]=[CH:20][C:21]4[C:27]5[C:28]([O:36][CH3:37])=[C:29]([O:34][CH3:35])[C:30]([O:32][CH3:33])=[CH:31][C:26]=5[CH2:25][CH2:24][C@H:23]([NH:38][C:39](=[O:41])[CH3:40])[C:22]=4[CH:42]=3)=[O:16])=[CH:19][CH:20]=2)[CH2:58][CH2:57]1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 531671-MethylpiperazineHCID 69586384(5S)-5-(acetylamino)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-yl 3-{[(2R)-2,6-di(tertbutoxycarbonylamino)hexanoyl]amino}propanoate

Product 1

HCID 58658583N-[(5S)-3-(4-{4-methylpiperazin-1-ylmethyl}phenylcarbonyloxy)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl]acetamideYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of N-[(5S)-3-(4-chloromethylphenylcarbonyloxy)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl]acetamide (1) (0.308 g; 0.604 mmol), 1-methylpiperazine (0.088 ml; 0.785 mmol) and sodium iodide (0.02 g; 0.121 mmol) in acetonitrile (10 ml) was stirred under argon atmosphere overnight. After evaporation to dryness, the residue was purified by flash chromatography eluting with a 5–12% gradient of methanol/dichloromethane. After evaporation of the appropriate fractions, the solid was triturated in ether/pentane to give N-[(5S)-3-(4-{4-methylpiperazin-1-ylmethyl}phenylcarbonyloxy)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl]acetamide as a solid.

Workup

  1. customAfter evaporation to dryness
  2. customthe residue was purified by flash chromatography
  3. washeluting with a 5–12% gradient of methanol/dichloromethane
  4. customAfter evaporation of the appropriate fractions
  5. customthe solid was triturated in ether/pentane

Sources & evidence

ORD record
ord-47f9f980937c43ff8ad242773b7969f1
Source dataset
uspto-grants-2006_11
Patent number
US07135502B1

Reaction notes

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