Methyl iodide → HCID 11348311, compound

HRID 2095529Notes

Reaction equation

HRID 2095529 reaction equation
I[CH3:2].[C:3]([O:7][C:8](=[O:25])[CH2:9][CH2:10][C@H:11]([NH:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[CH2:12][OH:13])([CH3:6])([CH3:5])[CH3:4]>C(#N)C.[Ag-]=O>[C:3]([O:7][C:8](=[O:25])[CH2:9][CH2:10][C@H:11]([NH:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[CH2:12][O:13][CH3:2])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 15043091HCID 15043091, compound

Product 1

HCID 11348311HCID 11348311, compoundYield 65.4%

Reagents, catalysts & solvents 2

HCID 178418778HCID 178418778, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of 4.82 ml (77.3 mmol) of iodomethane and 2.50 g (7.7 mmol) (S)-4-Benzyloxycarbonylamino-5-hydroxy-pentanoic acid tert-butyl ester in 25 ml of acetonitrile was cooled (0° C.) and treated with 2.72 g (11.8 mmol) of silver(I) oxide. The reaction mixture was stirred at RT for 3 days. The reaction was filtered and evaporated to yield after flash chromatography (SiO2, dichloromethane/ether 2.5%) 1.70 g (65%) of the titled compound as light yellow oil. MS: 360.18 (M+Na).

Workup

  1. filtrationThe reaction was filtered
  2. customevaporated

Sources & evidence

ORD record
ord-2193084065314a61b495b3189c7bc003
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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