Methyl iodide → HCID 11359854, compound

HRID 3058

Reaction equation

HRID 3058 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].[C:25](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[CH3:1][O:2][C:3](=[O:24])[C@H:4]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:23][CH3:25])=[CH:21][CH:22]=1)[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 7010613N-[(Phenylmethoxy)carbonyl]-L-tyrosine methyl ester

Product 1

HCID 11359854HCID 11359854, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

32.94 g (100 mmol) of N-benzyloxycarbonyl-tyrosine methyl ester is mixed in 200 ml of DMF with 27.64 g (200 mmol) of ground potassium carbonate. 15.6 g (110 mmol) of iodomethane is instilled in this suspension and stirred overnight at room temperature. The solution is concentrated by evaporation, dispersed between ethyl acetate and water, and the organic phase is mixed with hexane after drying (Na2SO4). The title compound crystallizes out.

Workup

  1. concentrationThe solution is concentrated by evaporation
  2. additiondispersed between ethyl acetate and water
  3. additionthe organic phase is mixed with hexane
  4. dry with materialafter drying (Na2SO4)
  5. customThe title compound crystallizes out

Sources & evidence

ORD record
ord-dba6f3dde0664944932faac3af102356
Source dataset
uspto-grants-1998_03
Patent number
US05733522

Linked notes

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