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

HRID 449755

반응식

HRID 449755 반응식
[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

참가 물질

6

반응물 2

HCID 790982,5-Dimethoxytetrahydrofuran2회HCID 6994982methyl (2S)-2-amino-6-(phenylmethoxycarbonylamino)hexanoate

생성물 1

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

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

반응 조건

온도
110 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-6d9649b7421447f4a7a6b7819e714072
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486534B2

연결된 노트

불러오는 중…