1,1-Dimethylethyl 15-azido-4,7,10,13-tetraoxapentadecanoate → tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate

HRID 2083892노트

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HRID 2083892 반응식
[C:1]([O:5][C:6](=[O:24])[CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][N:21]=[N+]=[N-])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:24])[CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][NH2:21])([CH3:2])([CH3:4])[CH3:3]

참가 물질

4

반응물 1

HCID 534861401,1-Dimethylethyl 15-azido-4,7,10,13-tetraoxapentadecanoate

생성물 1

HCID 51340928tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate수율 89.4%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

The crude material 18a (3.0 g, 8.0 mmol) was dissolved in ethanol (20 mL) and 300 mg of 10% Pd/C was added. The system was evacuated under vacuum and placed under 1 atm of hydrogen gas via balloon with vigorous stirring, and repeated 4 times to ensure a pure hydrogen atmosphere. The reaction was then stirred overnight at room temperature. TLC showed that the reaction was complete after 16 hrs. The crude reaction was passed through a short pad of celite rinsing with ethyl acetate. The solvent was removed and the amine purified on silica gel using a mixture of 15% methanol and 2.5% triethylamine in methylene chloride as the eluant to give 2.3 g (85% yield) of the desired amine 19a (FIG. 8). 1H NMR: 1.36 (s, 9H), 2.27 (br s., 2H), 2.42 (t, 2H, J=6.4 Hz), 2.80 (t, 2H, J=5.2 Hz), 3.45 (d, 2H, J=5.2 Hz), 3.51-3.59 (m, 12H), 3.63 (d, 2H, J=6.4 Hz). MS: m/z Calculated: 322.21, Found: 321.97.

후처리

  1. customThe system was evacuated under vacuum
  2. waitwas complete after 16 hrs
  3. customThe crude reaction
  4. washrinsing with ethyl acetate
  5. customThe solvent was removed
  6. customthe amine purified on silica gel using
  7. additiona mixture of 15% methanol and 2.5% triethylamine in methylene chloride as the eluant

출처 및 근거

ORD 기록
ord-85790d7133be4c4a868f1c8953ca9d29
출처 데이터셋
uspto-grants-2004_04
특허 번호
US06716821B2

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