Benzyl Alcohol → Trans 2-benzyloxycarbonylamino-3-carboethoxy-1,2,3,4-tetrahydronaphthalene

HRID 901993노트

반응식

HRID 901993 반응식
[C:1]([C@H:6]1[C@H:15](C(O)=O)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)([O:3][CH2:4][CH3:5])=[O:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:26])C=CC=CC=1.C([N:38]([CH2:41]C)CC)C.[CH2:43]([OH:50])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.[Cl-].[NH4+]>[CH2:43]([O:50][C:41]([NH:38][C@H:15]1[C@H:6]([C:1]([O:3][CH2:4][CH3:5])=[O:2])[CH2:7][C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:14]1)=[O:26])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

참가 물질

8

반응물 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 58646746Trans 2-carboethoxy-3-carboxy-1,2,3,4-tetrahydronaphthalene

생성물 1

HCID 58646750Trans 2-benzyloxycarbonylamino-3-carboethoxy-1,2,3,4-tetrahydronaphthalene

시약·촉매·용매 3

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매HCID 25517Ammonium Chloride용매

반응 조건

온도
100 °C

실험 절차

To a stirred solution of trans 2-carboethoxy-3-carboxy-1,2,3,4-tetrahydronaphthalene (546 mg, 2.2 mmol) in toluene (15 mL) under nitrogen was added diphenylphosphoryl azide (0.62 mL, 2.86 mmol), triethylamine (0.4 mL, 2.86 mmol) and benzyl alcohol (1.14 mL, 11 mmol). The reaction mixture was heated to 100° C. for 19 h. The toluene was removed under vacuum to yield a residue. The residue was diluted with ethyl acetate and aqueous ammonium chloride solution. The organic layer was washed with 1.0 M aqueous hydrochloric acid solution, saturated aqueous sodium carbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated under vacuum to yield a residue. The residue was purified by silica gel chromatography (10% ethyl acetate in hexane was used) to obtain the title compound (800 mg, containing some benzyl alcohol). 13C NMR (500 MHz, CDCl3) δ 173.2, 155.5, 136.3, 133.5, 133.2, 129.0, 128.5, 128.1, 127.6, 126.9, 126.4, 126.3, 66.7, 65.3, 48.7, 45.3, 35.0, 30.4, 14.1. 1H NMR (400 MHz, CDCl3) δ 7.02-7.38 (m, 9H), 5.10 (s, 2H), 4.29 (m, 1H), 4.14 (m, 2H), 3.22 (m, 2H), 3.02 (dd, J=5.7, 17.2 Hz, 1H), 2.88 (m, 1H), 2.76 (dd, J=7.2, 16.8 Hz, 1H), 1.23 (t, J=7.0 Hz, 3H).

후처리

  1. customThe toluene was removed under vacuum
  2. customto yield a residue
  3. washThe organic layer was washed with 1.0 M aqueous hydrochloric acid solution, saturated aqueous sodium carbonate solution and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customto yield a residue
  7. customThe residue was purified by silica gel chromatography (10% ethyl acetate in hexane was used)

출처 및 근거

ORD 기록
ord-2b54ac2ac3234f01a1dd52de41150b0f
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07365061B2

반응 노트

불러오는 중…