Sodium Bicarbonate → 3-(3-(((9H-fluoren-9-yl)methoxy)carbonylamino)propanamido)-4-((2S,3R,4S,5S,6S)-3,4,5-triacetoxy-6-(methoxycarbonyl)-tetrahydro-2H-pyran-2-yloxy)benzyl 2-(3-hydroxypropyl)oxazolidine-3-carboxylate

HRID 1395850노트

반응식

HRID 1395850 반응식
[Si]([O:18][CH2:19][CH2:20][CH2:21][CH:22]1[N:26]([C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][C@H:38]3[C@H:43]([O:44][C:45](=[O:47])[CH3:46])[C@@H:42]([O:48][C:49](=[O:51])[CH3:50])[C@H:41]([O:52][C:53](=[O:55])[CH3:54])[C@@H:40]([C:56]([O:58][CH3:59])=[O:57])[O:39]3)=[C:33]([NH:60][C:61](=[O:82])[CH2:62][CH2:63][NH:64][C:65]([O:67][CH2:68][CH:69]3[C:81]4[CH:80]=[CH:79][CH:78]=[CH:77][C:76]=4[C:75]4[C:70]3=[CH:71][CH:72]=[CH:73][CH:74]=4)=[O:66])[CH:32]=2)=[O:28])[CH2:25][CH2:24][O:23]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C1COCC1.N1C=CC=CC=1>[OH:18][CH2:19][CH2:20][CH2:21][CH:22]1[N:26]([C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][C@H:38]3[C@H:43]([O:44][C:45](=[O:47])[CH3:46])[C@@H:42]([O:48][C:49](=[O:51])[CH3:50])[C@H:41]([O:52][C:53](=[O:55])[CH3:54])[C@@H:40]([C:56]([O:58][CH3:59])=[O:57])[O:39]3)=[C:33]([NH:60][C:61](=[O:82])[CH2:62][CH2:63][NH:64][C:65]([O:67][CH2:68][CH:69]3[C:70]4[CH:71]=[CH:72][CH:73]=[CH:74][C:75]=4[C:76]4[C:81]3=[CH:80][CH:79]=[CH:78][CH:77]=4)=[O:66])[CH:32]=2)=[O:28])[CH2:25][CH2:24][O:23]1

참가 물질

5

반응물 2

HCID 516892Sodium BicarbonateHCID 598165413-(3-(((9H-fluoren-9-yl)methoxy)carbonylamino)propanamido)-4-((2S,3R,4S,5S,6S)-3,4,5-triacetoxy-6-(methoxycarbonyl)-tetrahydro-2H-pyran-2-yloxy)benzyl 2-(3-(tert-butyldiphenylsilyloxy)propyl)oxazolidine-3-carboxylate

생성물 1

HCID 866234303-(3-(((9H-fluoren-9-yl)methoxy)carbonylamino)propanamido)-4-((2S,3R,4S,5S,6S)-3,4,5-triacetoxy-6-(methoxycarbonyl)-tetrahydro-2H-pyran-2-yloxy)benzyl 2-(3-hydroxypropyl)oxazolidine-3-carboxylate수율 94.6%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of the silyl ether 13 (52 mg, 0.042 mmol) in THF (2 mL) and pyridine (2 mL) was added HF-pyridine complex (400 μL). The reaction mixture was stirred for 3 h and was poured into saturated aqueous sodium bicarbonate and was extracted with ethyl acetate (3×100 mL). The combined extracts were washed with water and brine and dried over sodium sulfate, before being filtered and concentrated. The resulting oil was purified via radial chromatography on a 1 plate eluting with 5% methanol in dichloromethane to give 36 mg (86%) of a solid residue: 1H NMR (CD3OD); δ1.55 (bs, 2H), 1.68 (m, 1H), 1.87 (m, 1H), 1.95 (s, 3H), 2.01 (m, 6H), 2.67 (oct, 2H, J=6.8 Hz), 3.30 (m, 1H), 3.50 (m, 3H), 3.65 (m, 1H), 3.69 (m, 3H), 3.82 (q, 1H, J=8.0 Hz), 4.01 (m, 1H), 4.23 (m, 1H, J=7.0 Hz), 4.25-4.40 (m, 2H), 4.47 (d, 1H, J=10.0 Hz), 5.0-5.15 (m, 3H), 5.19 (t, 1H, J=9.8 Hz), 5.28 (dd, 1H, J=6.0, 9.6 Hz), 5.39 (d, 1H, J=7.6 Hz), 5.49 (m, 3H), 7.11 (m, 2H), 7.17-7.32 (m, 3H), 7.34 (t, 2H, J=7.4 Hz), 7.62 (d, 2H, J=7.6 Hz), 7.77 (d, 2H, J=7.6 Hz), 8.07 (s, 1H); LC-MS m/z (ES+), 927.87 (M+Na+)+, 9.79 min.

후처리

  1. additionwas added HF-pyridine complex (400 μL)
  2. extractionwas extracted with ethyl acetate (3×100 mL)
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationbefore being filtered
  6. concentrationconcentrated
  7. customThe resulting oil was purified via radial chromatography on a 1 plate
  8. washeluting with 5% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-0bf4611abf5f41f3ad5b0bb8b8687475
출처 데이터셋
uspto-grants-2014_12
특허 번호
USRE045272E1

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