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Benzyl Alcohol → benzyl (3R,4S)-4-[(tert-butoxycarbonyl)amino]-3-hydroxy-5-phenyl-1-[4-(2-pyridinyl)benzyl]pentylcarbamate

HRID 1174284
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HRID 1174284 반응식
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C@H:10]([O:29][Si](C(C)(C)C)(C)C)[CH2:11][CH:12]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)=[CH:19][CH:18]=1)C(O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:51])=CC=1.C([N:63]([CH2:66]C)CC)C.[CH2:68]([OH:75])[C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C@H:10]([OH:29])[CH2:11][CH:12]([NH:63][C:66](=[O:51])[O:75][CH2:68][C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1)[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)=[CH:19][CH:18]=1)=[O:7])([CH3:3])([CH3:2])[CH3:4]
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참가 물질

6

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HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 67407170(4R,5S)-5-[(tert-butoxycarbonyl)amino]-4-{[tert-butyl(dimethyl)silyl]oxy}-6-phenyl-2-[4-(2-pyridinyl)benzyl]hexanoic acid

생성물 1

HCID 86726218benzyl (3R,4S)-4-[(tert-butoxycarbonyl)amino]-3-hydroxy-5-phenyl-1-[4-(2-pyridinyl)benzyl]pentylcarbamate
수율 37.4%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
25 °C

실험 절차

A solution of the product from Example 107C (22.35 mmol) in toluene (500 mL) was treated with DPPA (5.3 mL, 24.59 mmol) and triethylamine (3.75 mL, 26.90 mmol) was heated at reflux for 2 hours, cooled to 25° C., treated with benzyl alcohol (6.9 mL, 66.68 mmol), heated at reflux for an additional 16 hours, cooled and concentrated. A solution of the concentrate in THF (100 mL) was treated with TBAF solution in THF (67 mL, 1N), stirred at 25° C. for 40 hours, concentrated, and partitioned between ethyl acetate and water. The organic phase was washed with brined, dried over MgSO4, filtered and concentrated, to give the title compound (4.98 g, 37% yield), which was used without further purification.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. temperatureheated
  4. temperatureat reflux for an additional 16 hours
  5. temperaturecooled
  6. concentrationconcentrated
  7. concentrationA solution of the concentrate in THF (100 mL)
  8. additionwas treated with TBAF solution in THF (67 mL, 1N)
  9. concentrationconcentrated
  10. custompartitioned between ethyl acetate and water
  11. washThe organic phase was washed with brined,
  12. dry with materialdried over MgSO4
  13. filtrationfiltered
  14. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c9a559c4f854421293b62f43d2d9bcd9
출처 데이터셋
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07834043B2

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