2,5-Dimethoxytetrahydrofuran → (S)-methyl 6-benzyloxycarbonylamino-2-carbazol-9-yl-hexanoate

HRID 449755

反応式

HRID 449755 の反応式
[NH2:1][C@H:2]([C:18]([O:20][CH3:21])=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].CO[CH:24]1[CH2:28][CH2:27][CH:26](OC)O1>C(O)(=O)C.O1CCOCC1.ClCCl>[CH2:11]([O:10][C:8]([NH:7][CH2:6][CH2:5][CH2:4][CH2:3][C@H:2]([N:1]1[C:24]2[CH:4]=[CH:3][CH:2]=[CH:18][C:28]=2[C:27]2[C:26]1=[CH:27][CH:28]=[CH:24][CH:26]=2)[C:18]([O:20][CH3:21])=[O:19])=[O:9])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

6

反応物 2

HCID 790982,5-Dimethoxytetrahydrofuran2 回HCID 6994982methyl (2S)-2-amino-6-(phenylmethoxycarbonylamino)hexanoate

生成物 1

HCID 67993166(S)-methyl 6-benzyloxycarbonylamino-2-carbazol-9-yl-hexanoate収率 49.5%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

A vigorously stiffed solution of L-Lys(Z)—OMe (3.31 g, 10 mmol) in acetic acid (20 mL) and dioxane (40 mL) was heated to 75° C., at this temperature 2,5-dimethoxytetrahydrofuran (DMTHF, ee 97%) (3.97 g, 3.90 mL, 30 mmol) was added dropwise to the reaction mixture. After complete addition of DMTHF, the reaction mixture was refluxed at 110° C. for 3 h followed by 5-6 h stiffing at room temperature. The volatiles were removed under reduced pressure to afford a dark brown residue, which was dissolved in dichloromethane (100 mL) and washed with 10% NaHCO3 solution (15 mL), brine (15 mL) and water (15 mL). The organic phase was dried over anhydrous Na2SO4 and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (230-400 mesh) using hexane:ethyl acetate (7:3) as eluent to afford (S)-methyl 6-benzyloxycarbonylamino-2-carbazol-9-yl-hexanoate 3 (1.10 g, 25%) as a pale yellow solid.

後処理

  1. additionwas added dropwise to the reaction mixture
  2. customstiffing at room temperature
  3. customThe volatiles were removed under reduced pressure
  4. customto afford a dark brown residue, which
  5. washwashed with 10% NaHCO3 solution (15 mL), brine (15 mL) and water (15 mL)
  6. dry with materialThe organic phase was dried over anhydrous Na2SO4
  7. customevaporated under reduced pressure
  8. customThe residue was purified by flash chromatography on silica gel (230-400 mesh)

出典と根拠

ORDレコード
ord-6d9649b7421447f4a7a6b7819e714072
出典データセット
uspto-grants-2013_07
特許番号
US08486534B2

関連ノート

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