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

HRID 343038

反応式

HRID 343038 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒2 回

実験手順

Cesium carbonate (4.28 g., 13.1 mmoles) was added to a mixture of N2 -[(1,1-dimethylethoxy) carbonyl]-N6 -[(phenylmethoxy)carbonyl]-L-lysine (10 g., 26.3 mmoles) 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 (3x). 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).

後処理

  1. customthe residual water removed azeotropically with acetonitrile (3x)
  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

出典と根拠

ORDレコード
ord-948bd0bdab1141bf8ef3c4f1c6097bdb
出典データセット
uspto-grants-1999_01
特許番号
US05859239

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