Dimethylformamide → tert-butyl 4-{3-[(3R)-3-{[(1S)-3-tert-butoxy-1-(5-{2-[3-(2-{[(4-methylphenyl)sulfonyl]oxy}ethoxy)phenyl]ethyl}pyridin-3-yl)-3-oxopropyl]carbamoyl}piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate

HRID 526394ノート

反応式

HRID 526394 の反応式
[C:1]([O:5][C:6](=[O:50])[CH2:7][C@H:8]([NH:24][C:25]([C@@H:27]1[CH2:32][CH2:31][CH2:30][N:29]([C:33](=[O:49])[CH2:34][CH2:35][CH:36]2[CH2:41][CH2:40][N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:38][CH2:37]2)[CH2:28]1)=[O:26])[C:9]1[CH:10]=[N:11][CH:12]=[C:13]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=2)[CH:14]=1)([CH3:4])([CH3:3])[CH3:2].[C:51](=[O:54])([O-])[O-].[Cs+].[Cs+].[CH3:57][C:58]1[CH:63]=[CH:62][C:61]([S:64]([O-:67])(=O)=[O:65])=[CH:60][CH:59]=1.[CH3:68]N(C)C=O>>[C:1]([O:5][C:6](=[O:50])[CH2:7][C@H:8]([NH:24][C:25]([C@@H:27]1[CH2:32][CH2:31][CH2:30][N:29]([C:33](=[O:49])[CH2:34][CH2:35][CH:36]2[CH2:41][CH2:40][N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:38][CH2:37]2)[CH2:28]1)=[O:26])[C:9]1[CH:10]=[N:11][CH:12]=[C:13]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:68][CH2:51][O:54][S:64]([C:61]3[CH:62]=[CH:63][C:58]([CH3:57])=[CH:59][CH:60]=3)(=[O:67])=[O:65])[CH:18]=2)[CH:14]=1)([CH3:3])([CH3:2])[CH3:4]

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 85570p-ToluenesulfonateHCID 71258963Tert-butyl 4-{3-[(3R)-3-{[(1S)-3-tert-butoxy-1-{5-[(3-hydroxyphenyl)ethyl]pyridin-3-yl}-3-oxopropyl]carbamoyl}piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate

生成物 1

HCID 71609688tert-butyl 4-{3-[(3R)-3-{[(1S)-3-tert-butoxy-1-(5-{2-[3-(2-{[(4-methylphenyl)sulfonyl]oxy}ethoxy)phenyl]ethyl}pyridin-3-yl)-3-oxopropyl]carbamoyl}piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate

実験手順

Tert-butyl 4-{3-[(3R)-3-{[(1S)-3-tert-butoxy-1-{5-[(3-hydroxyphenyl)ethyl]pyridin-3-yl}-3-oxopropyl]carbamoyl}piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate (67 mg, 0.10 mmol) was dissolved in N,N-dimethylformamide (9.7 mL). Cesium carbonate (79 mg, 0.24 mmol) and ethane-1,2-diyl bis(4-methylbenzenesulfonate (54 mg, 0.15 mmol) were added. The mixture was stirred at room temperature for 4 hours, quenched by addition of saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The combined extracts were washed with brine and dried over sodium sulfate. The solution was concentrated under reduced pressure and the residue was purified by chromatography on silica gel (ethyl acetate in hexane 20% to 100% followed by dioxane in ethyl acetate 0 to 50%) to yield 49 mg of tert-butyl 4-{3-[(3R)-3-{[(1S)-3-tert-butoxy-1-(5-{2-[3-(2-{[(4-methylphenyl)sulfonyl]oxy}ethoxy)phenyl]ethyl}pyridin-3-yl)-3-oxopropyl]carbamoyl}piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate.

後処理

  1. customquenched by addition of saturated aqueous ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationThe solution was concentrated under reduced pressure
  6. customthe residue was purified by chromatography on silica gel (ethyl acetate in hexane 20% to 100% followed by dioxane in ethyl acetate 0 to 50%)

出典と根拠

ORDレコード
ord-3b7186fa06f84f4e8f30572f707245c7
出典データセット
uspto-grants-2016_05
特許番号
US09345793B2

反応ノート

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