Dichloromethane → tert-butyl (1S)-1-[4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)benzyl]-2-hydroxyethylcarbamate

HRID 724600ノート

反応式

HRID 724600 の反応式
[OH:1][CH2:2][C@H:3]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:4][C:5]1[CH:10]=[CH:9][C:8](B2OC(C)(C)C(C)(C)O2)=[CH:7][CH:6]=1.[C:28]([N:32]1[C:36](=[O:37])[CH:35]=[C:34](Cl)[S:33]1(=[O:40])=[O:39])([CH3:31])([CH3:30])[CH3:29].C(=O)([O-])[O-].[K+].[K+].ClCCl>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:28]([N:32]1[C:36](=[O:37])[CH:35]=[C:34]([C:8]2[CH:7]=[CH:6][C:5]([CH2:4][C@H:3]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[CH2:2][OH:1])=[CH:10][CH:9]=2)[S:33]1(=[O:39])=[O:40])([CH3:31])([CH3:29])[CH3:30]

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 218786382-Tert-butyl-5-chloro-2,3-dihydro-1lambda6,2-thiazole-1,1,3-trioneHCID 86602075tert-butyl {(1R)-2-hydroxy-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]ethyl}carbamate

生成物 1

HCID 58746779tert-butyl (1S)-1-[4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)benzyl]-2-hydroxyethylcarbamate収率 163.5%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

Combined 34-A (6.1 g, 61 mmol), 9-A (3.55 g, 15.9 mmol), potassium carbonate (10.0 g, 72.4 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (2.50 g, 3.06 mmol) in 200 mL dioxane. The reaction was degassed and heated at 90° C. for 48 hours. The crude was extracted with ethyl acetate, washed with water and brine. The combined organic extracts were dried over Na2SO4, filtered and evaporated to give 11.4 g of a dark glass. The crude was chromatographed on a silica column to afford a dark semi-solid (3.3 g, 90%). 1H NMR (500 MHz, CDCl3): δ 7.72 (d, J=8.8 Hz, 2H), 7.38 (d, J=8.8 Hz, 2H), 6.62 (s, 1H), 4.77 (br s, 1H), 3.89 (br s, 1H), 3.69 (m, 1H), 3.58 (m, 1H), 2.93 (d, J=7.2 Hz, 2H) 1.43 (s, 9H), 1.39 (s, 9H).

後処理

  1. customThe reaction was degassed
  2. extractionThe crude was extracted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-ac51c16b69c94d40bc327f6d397a29e2
出典データセット
uspto-grants-2006_11
特許番号
US07141596B2

反応ノート

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