Methyl iodide → N2 [(1,1-Dimethylethoxy)carbonyl]-N6-[(phenylmethoxy)carbonyl]-L-lysine, methyl ester

HRID 1320

Reaction equation

HRID 1320 reaction equation
[C:1](=O)([O-])[O-].[Cs+].[Cs+].[N:7]#[N:8].[CH3:9][C:10]([CH3:35])([O:12][C:13]([NH:15][C@H:16]([C:32]([OH:34])=[O:33])[CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])=[O:14])[CH3:11].O.CO.CI>C(OCC)(=O)C>[N:7]#[N:8].[CH3:11][C:10]([CH3:35])([O:12][C:13]([NH:15][C@H:16]([C:32]([O:34][CH3:1])=[O:33])[CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]([O:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:23])=[O:14])[CH3:9]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 22242641Methanol--water (1/1)HCID 86742311N2 [(1,1-dimethylethoxy)carbonyl]-N6-[(phenylmethoxy)carbonyl]-L-lysine

Product 1

HCID 131714291N2 [(1,1-Dimethylethoxy)carbonyl]-N6-[(phenylmethoxy)carbonyl]-L-lysine, methyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Cesium carbonate (4.28 g., 13.1 moles) was added to a mixture of N2 -[(1,1-dimethylethoxy)carbonyl]-N6 -[(phenylmethoxy)carbonyl]-L-lysine (10 g., 26.3 moles) and 20% water-methanol (60 ml.). The solution became homogeneous within 5 minutes so the solvent was stripped and the residual water removed azeotropically with acetonitrile (3×). The resulting oil was dried in vacuo, dissolved in dry dimethyl-formamide and treated with methyl iodide (3.2 ml., 2.0 eq.). The reaction mixture was stirred at room temperature for 1.5 hours under argon, diluted with ethyl acetate (200 ml.) and washed successively with water (2×25 ml.), saturated sodium bicarbonate (25 ml.) and brine (25 ml.). The organic phase was dried (anhydrous magnesium sulfate), filtered, evaporated to dryness and dried in vacuo to give 10.11 g., of product as a light yellow syrup; Rf =0.30 (ethyl acetate:hexanes, 1:2).

Workup

  1. customthe residual water removed azeotropically with acetonitrile (3×)
  2. customThe resulting oil was dried in vacuo
  3. dissolutiondissolved in dry dimethyl-formamide
  4. washwashed successively with water (2×25 ml.), saturated sodium bicarbonate (25 ml.) and brine (25 ml.)
  5. dry with materialThe organic phase was dried (anhydrous magnesium sulfate)
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customdried in vacuo
  9. customto give 10.11 g

Sources & evidence

ORD record
ord-a5a96d1b986849b2b488b84cd2b4e308
Source dataset
uspto-grants-1998_03
Patent number
US05723602

Linked notes

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