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

HRID 484758

반응식

HRID 484758 반응식
[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].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]

참가 물질

6

반응물 4

HCID 887Methanol2회HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 86742311N2 [(1,1-dimethylethoxy)carbonyl]-N6-[(phenylmethoxy)carbonyl]-L-lysine

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

Cesium carbonate (2.14 g., 6.55 mmole) is added to a mixture of N2 -[(1,1-dimethylethoxy)carbonyl]-N6 -[(phenylmethoxy)carbonyl]-L-lysine (5.0 g., 13.10 mmole) and 20% aqueous methanol (30 ml.). The solution becomes homogeneous after 5 minutes, the methanol is stripped, and the residual water is removed azetropically with acetonitrile (twice). The resulting oil is taken up in dry methylene chloride (10 ml.) and treated with methyl iodide (1.6 ml., 2.0 eq.) at 25° in an argon atmosphere. After 4 hours the reaction mixture is taken up in ethyl acetate and washed successively with water, saturated sodium bicarbonate and brine, dried (MgSO4), and evaporated. The residue (4.7 g.) is chromatographed on silica (160 g.) eluting with hexane/ethyl acetate (3:1) to give 4.0 g. of N2 -[(1,1-dimethylethoxy)carbonyl]-N6 -[(phenylmethoxy)carbonyl]-L-lysine, methyl ester as an oil after evaporation. TLC (hexane/ethyl acetate; 2:1) major spot at Rf =0.3.

후처리

  1. customthe residual water is removed azetropically with acetonitrile (twice)
  2. washwashed successively with water, saturated sodium bicarbonate and brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue (4.7 g.) is chromatographed on silica (160 g.)
  6. washeluting with hexane/ethyl acetate (3:1)
  7. customto give 4.0 g
  8. customof N2 -[(1,1-dimethylethoxy)carbonyl]-N6 -[(phenylmethoxy)carbonyl]-L-lysine, methyl ester as an oil after evaporation

출처 및 근거

ORD 기록
ord-07fbc4c8362c439f8c44466c7c1c52f8
출처 데이터셋
uspto-grants-1985_08
특허 번호
US04533661

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