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Ammonium formate → ((2S,3R,4S)-4-Amino-4-(2,4-difluorophenyl)-2-((trityloxy)methyl)tetrahydrofuran-3-yl)methanol

HRID 68372
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[NH2:1][C@@:2]1([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[C:32](Cl)[C:31]=2[F:38])[CH2:6][O:5][C@H:4]([CH2:7][O:8][C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C@H:3]1[CH2:28][OH:29].C([O-])=O.[NH4+]>[Pd].CO>[NH2:1][C@@:2]1([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=2[F:38])[CH2:6][O:5][C@H:4]([CH2:7][O:8][C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C@H:3]1[CH2:28][OH:29]
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참가 물질

5

반응물 2

HCID 2723923Ammonium formateHCID 86707811((2S,3R,4S)-4-Amino-4-(3-chloro-2,4-difluorophenyl)-2-((trityloxy)methyl)tetrahydrofuran-3-yl)methanol

생성물 1

HCID 86707812((2S,3R,4S)-4-Amino-4-(2,4-difluorophenyl)-2-((trityloxy)methyl)tetrahydrofuran-3-yl)methanol수율 99.2%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887
Methanol
용매

실험 절차

A mixture of ((2S,3R,4S)-4-amino-4-(3-chloro-2,4-difluorophenyl)-2-((trityloxy)methyl)tetrahydrofuran-3-yl)methanol (4.49 g, 8.4 mmol), ammonium formate (3.2 g, 50 mmol) and 10% palladium on carbon (500 mg) in dry MeOH (40 mL) was stirred at RT under nitrogen overnight. The catalyst was removed by filtration through Celite®—washing with methanol. The filtrate was evaporated and the residue was partitioned between DCM (100 mL) and saturated aqueous NaHCO3 (50 mL). The layers were separated and the aqueous layer was further extracted with DCM (100 mL×4). The combined extracts were dried (Na2SO4), filtered and evaporated to give the title compound (4.18 g). 1H NMR (400 MHz, MeOH-d4) δ ppm: 2.73-2.84 (m, 1 H) 3.17 (dd, J=10.03, 5.14 Hz, 1 H) 3.27 (dd, J=9.96, 3.61 Hz, 1 H) 3.65-3.79 (m, 2 H) 3.88 (dd, J=8.93, 3.06 Hz, 1 H) 4.16-4.24 (m, 1 H) 4.27 (d, J=9.05 Hz, 1 H) 6.88-7.00 (m, 2 H) 7.18-7.31 (m, 9 H) 7.38-7.45 (m, 6 H) 7.58-7.67 (m, 1 H).

후처리

  1. customThe catalyst was removed by filtration through Celite®—washing with methanol
  2. customThe filtrate was evaporated
  3. customthe residue was partitioned between DCM (100 mL) and saturated aqueous NaHCO3 (50 mL)
  4. customThe layers were separated
  5. extractionthe aqueous layer was further extracted with DCM (100 mL×4)
  6. dry with materialThe combined extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated

출처 및 근거

ORD 기록
ord-86562488654041a6b254a048b24267f5
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08822455B2

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