Methyl iodide → HCID 69424963, compound

HRID 1182244Notes

Reaction equation

HRID 1182244 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]2[CH:13]([CH2:33][OH:34])[CH:14]([N:16]3[CH2:20][CH2:19][CH:18]([NH:21][C:22]([O:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[O:23])[C:17]3=[O:32])[CH2:15][CH:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].I[CH3:36]>[Ag]=O.CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]2[CH:13]([CH2:33][O:34][CH3:36])[CH:14]([N:16]3[CH2:20][CH2:19][CH:18]([NH:21][C:22]([O:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[O:23])[C:17]3=[O:32])[CH2:15][CH:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 69424008HCID 69424008, compound

Product 1

HCID 69424963HCID 69424963, compound

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-(3-benzyloxycarbonylamino-2-oxo-pyrrolidin-1-yl)-4-hydroxymethyloctahydrocyclopenta[c]-pyrrole-2-carboxylic acid tert-butyl ester in a small amount of DMF and a large excess of iodomethane is treated with silver oxide and stirred at room temperature until the reaction is complete. Upon completion of the reaction, the reaction mixture is filtered through celite and concentrated under vacuum yielding a residue. The residue is purified by flash column chromatography providing the title product.

Workup

  1. customUpon completion of the reaction
  2. filtrationthe reaction mixture is filtered through celite
  3. concentrationconcentrated under vacuum
  4. customyielding a residue
  5. customThe residue is purified by flash column chromatography

Sources & evidence

ORD record
ord-e3167d575f2544d684a3f42d1138a616
Source dataset
uspto-grants-2007_10
Patent number
US07288563B2

Reaction notes

Loading…