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Tetrabutylammonium Fluoride → benzyl (1S,3S,4S)-4-[(tert-butoxymethyl)amino]-3-hydroxy-1-[4-(6-methoxy-2-pyridinyl)benzyl]-5-phenylpentylcarbamate

HRID 1174310
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HRID 1174310 반응식
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[C@@H:10]([O:39][Si](C(C)(C)C)(C)C)[CH2:11][C@@H:12]([NH:28][C:29](=[O:38])[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[N:21]=2)=[CH:16][CH:15]=1)=O)([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:1]([O:5][CH2:6][NH:8][C@@H:9]([CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[C@@H:10]([OH:39])[CH2:11][C@@H:12]([NH:28][C:29](=[O:38])[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[N:21]=2)=[CH:16][CH:15]=1)([CH3:4])([CH3:2])[CH3:3]
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참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 86726222benzyl (1S,3S,4S)-4-[(tert-butoxycarbonyl)amino]-3-{[tert-butyl(dimethyl)silyl]oxy}-1-[4-(6-methoxy-2-pyridinyl)benzyl]-5-phenylpentylcarbamate

생성물 1

HCID 86726223benzyl (1S,3S,4S)-4-[(tert-butoxymethyl)amino]-3-hydroxy-1-[4-(6-methoxy-2-pyridinyl)benzyl]-5-phenylpentylcarbamate수율 32.1%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

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온도
25 °C

실험 절차

The product from Example 113B (0.28 mmol) was treated with TBAF solution in THF (1.4 mL, 1N), stirred at 25° C. for 16 hours, concentrated and partitioned between ethyl acetate and water. The organic phase was washed with brined, dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with 20% ethyl acetate in dichloromethane, to give the title compound (0.055 g, 31% yield).

후처리

  1. concentrationconcentrated
  2. custompartitioned between ethyl acetate and water
  3. washThe organic phase was washed with brined,
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel eluting with 20% ethyl acetate in dichloromethane

출처 및 근거

ORD 기록
ord-7728d5d305be4ef6a176583305f3677e
출처 데이터셋
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07834043B2

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