Methyl iodide → HCID 131716292, compound

HRID 330620Notes

Reaction equation

HRID 330620 reaction equation
[C:1]([NH:11][C@H:12]([C:14]([NH:16][C@H:17]([C:19]([NH:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[N:28]=[CH:27][CH:26]=[CH:25]2)=[O:20])[CH3:18])=[O:15])[CH3:13])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH3:32][I:33]>C(Cl)(Cl)Cl>[I-:33].[CH3:32][N:28]1[C:29]2[C:24](=[CH:23][C:22]([NH:21][C:19](=[O:20])[C@H:17]([CH3:18])[NH:16][C:14](=[O:15])[C@H:12]([CH3:13])[NH:11][C:1]([O:3][CH2:4][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=3)=[O:2])=[CH:31][CH:30]=2)[CH:25]=[CH:26][CH2:27]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 131716294HCID 131716294, compound

Product 1

HCID 131716292HCID 131716292, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 29 mg (0.06 mmol) of VII in 5 ml of chloroform was added 1 ml of methyliodide. After the mixture was stirred for 24 hours at room temperature, the solvent and alkylating agent were removed in vacuo to afford a thick orange oil. Crystallization from ethanol-ether produced 36 mg (90% yield), of a finely divided yellow powder: mp 135° C. decomposes; Rf(E)=0.06. Analysis calculated for C24H27N4O4I: C, 51.26; H, 4.84; N, 9.96. Found: C, 50.05; H, 5.23; N, 9.85. Fast atom bombardment mass spectrum: calculated for MW (435)+I-. Found: 435 (M+).

Workup

  1. customthe solvent and alkylating agent were removed in vacuo
  2. customto afford a thick orange oil
  3. customCrystallization from ethanol-ether
  4. customproduced 36 mg (90% yield)

Sources & evidence

ORD record
ord-23abeee68cbb4aab8b421e7f2967246d
Source dataset
uspto-grants-1990_01
Patent number
US04897444

Reaction notes

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