Trimethylsilyldiazomethane → HCID 18791582, compound

HRID 1005608Notes

Reaction equation

HRID 1005608 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:58]=[CH:57][CH:56]=[CH:55][C:14]=1[C:15]([NH:17][C:18]1[CH:49]=[CH:48][C:21]([C:22]([N:24]([CH3:47])[C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:26]=2[O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]([N:40]2[CH2:45][CH2:44][N:43]([CH3:46])[CH2:42][CH2:41]2)=[O:39])=[O:23])=[CH:20][C:19]=1[O:50][CH2:51][C:52]([OH:54])=[O:53])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:59][Si](C=[N+]=[N-])(C)C>CO>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:58]=[CH:57][CH:56]=[CH:55][C:14]=1[C:15]([NH:17][C:18]1[CH:49]=[CH:48][C:21]([C:22]([N:24]([CH3:47])[C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:26]=2[O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]([N:40]2[CH2:45][CH2:44][N:43]([CH3:46])[CH2:42][CH2:41]2)=[O:39])=[O:23])=[CH:20][C:19]=1[O:50][CH2:51][C:52]([O:54][CH3:59])=[O:53])=[O:16])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 18791518HCID 18791518, compound

Product 1

HCID 18791582HCID 18791582, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-[2-[(3-tert-butoxycarbonylaminoprop-1-yl)oxy]benzoyl]amino-3-carboxymethoxy-N-methyl-N-[2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]-4-methylphenyl]benzamide (128 mg) in methanol (5 ml) was added dropwise trimethylsilyldiazomethane (5 ml, 2.0M n-hexane solution) and stirred at ambient temperature for 30 minutes. The solution was concentrated in vacuo and the residue was purified by preparative thin layer silica gel chromatography (chloroform:methanol:28% aqueous ammonia solution, 50:5:1) to give 4-[2-[(3-tert-butoxycarbonylaminoprop-1-yl)oxy]benzoyl]amino-3-methoxycarbonylmethoxy-N-methyl-N-[2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]-4-methylphenyl]benzamide (85 mg).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthe residue was purified by preparative thin layer silica gel chromatography (chloroform:methanol:28% aqueous ammonia solution, 50:5:1)

Sources & evidence

ORD record
ord-82302aecb8fe4f6c80207d1d1d9439dd
Source dataset
uspto-grants-2000_04
Patent number
US06054457

Reaction notes

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