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Potassium Carbonate → Methyl 4-((2s)-2-{[(tert-butoxycarbonyl)((2s)-2-{[tert-butyl(dimethyl)silyl]oxy}-3-phenoxypropyl)amino]methyl}-3,4-dihydro-2h-chromen-6-yl)-2-hydroxybenzoate

HRID 47694
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HRID 47694 반응식
[Si:1]([O:8][C@H:9]([CH2:43][O:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[CH2:10][N:11]([CH2:19][C@@H:20]1[CH2:29][CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[C:25]([C:30]3[CH:31]=[CH:32][C:33]4[C:38](=[O:39])[O:37][C:36](C)(C)[O:35][C:34]=4[CH:42]=3)[CH:26]=2)[O:21]1)[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO>[C:14]([O:13][C:12]([N:11]([CH2:19][C@@H:20]1[CH2:29][CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[C:25]([C:30]3[CH:31]=[CH:32][C:33]([C:38]([O:37][CH3:36])=[O:39])=[C:34]([OH:35])[CH:42]=3)[CH:26]=2)[O:21]1)[CH2:10][C@H:9]([O:8][Si:1]([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:3])[CH3:2])[CH2:43][O:44][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)=[O:18])([CH3:15])([CH3:16])[CH3:17]
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참가 물질

4

반응물 2

HCID 11430Potassium CarbonateHCID 86587740tert-butyl (2S)-2-{[tert-butyl(dimethyl)silyl]oxy}-3-phenoxypropyl{[(2S)-6-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-7-yl)-3,4-dihydro-2H-chromen-2-yl]methyl}carbamate

생성물 1

HCID 69895945Methyl 4-((2s)-2-{[(tert-butoxycarbonyl)((2s)-2-{[tert-butyl(dimethyl)silyl]oxy}-3-phenoxypropyl)amino]methyl}-3,4-dihydro-2h-chromen-6-yl)-2-hydroxybenzoate수율 97%

시약·촉매·용매 1

HCID 887
Methanol
용매

실험 절차

To a solution of Example 204 (0.8 g, 1.14 mmol, 1.0 eq.) in methanol (10 mL) was added potassium carbonate (0.078 g, 0.57 mmol, 0.5 eq.) at room temperature. The reaction mixture was allowed to stir at room temperature for 18 hours and then concentrated under reduced pressure. The resulting residue was washed with distilled water (10 mL) and extracted with ethyl acetate (3×10 mL). The combined extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford the desired product as pale yellow oil (0.75 g, 97%). 1H NMR (CDCl3) δ10.68 (s, 1 H), 7.73 (d, 1H), 7.26-7.14 (m, 4H), 6.94 (dd, 1H), 6.86-6.75 (m, 5H), 4.21-4.02 (m, 2H), 3.83 (s, 3H), 3.80-3.56 (m, 4H), 3.40-3.21 (m, 2H), 2.80-2.67 (m, 2H), 1.95-1.92 (m, 1H), 1.65-1.60 (m, 1H), 1.38 (s, 9H), 0.83 (s, 9H), 0.001 (s, 6H).

후처리

  1. concentrationconcentrated under reduced pressure
  2. washThe resulting residue was washed with distilled water (10 mL)
  3. extractionextracted with ethyl acetate (3×10 mL)
  4. dry with materialThe combined extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-479d7073bf434ca5af8b75d104644ba6
출처 데이터셋
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06699860B2

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