Water → HCID 68648358, 화합물

HRID 1162530

반응식

HRID 1162530 반응식
[C:1]([O:5][C:6](=[O:22])[CH2:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:12][C:11]=1[Cl:21])=[O:9])([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[K+].O.[CH3:34][C:35]#[N:36]>>[C:1]([O:5][C:6]([C:7]1[C:35]([C:34]2[CH:11]=[CH:10][CH:8]=[CH:7][CH:6]=2)=[N:36][O:9][C:8]=1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:12][C:11]=1[Cl:21])=[O:22])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 4

HCID 962WaterHCID 6342Acetonitrile2회HCID 3251421Potassium bis(trimethylsilyl)amideHCID 686481833-(2-Chloro-4-methoxycarbonylmethyl-phenyl)-3-oxo-propionic acid tert-butyl ester

생성물 1

HCID 68648358HCID 68648358, 화합물

실험 절차

Intermediate 56 (115 mg, 0.35 mmol) is dissolved in MeCN (3 mL). Potassium bis(trimethylsilyl)amide (106 mg, 0.53 mmol) is added slowly while stirring at room temperature. Then the mixture is cooled to 0° C., and a solution of intermediate 58 (55 mg, 0.35 mmol) in CH3CN (1 mL) is added. The mixture is stirred at room temperature overnight, then H2O (5 mL) is added and the mixture is extracted with DCM (3×10 mL). After concentration the crude product is purified on reverse phase HPLC (H2O/MeCN gradient) to afford 5-(2-chloro-4-methoxycarbonylmethyl-phenyl)-3-phenyl-isoxazole-4-carboxylic acid tert-butyl ester 59 as a white solid: 1H-NMR (400 MHz, CDCl3) δ=7.73 (m, 2H), 7.47 (m, 5H), 7.33 (m, 1H), 3.72 (s, 3H), 3.68 (s, 2H), 1.23 (s, 9H). MS calculated for C23H23ClNO5 (M+H+) 428.1, found 428.1.

후처리

  1. temperatureThen the mixture is cooled to 0° C.
  2. stirringThe mixture is stirred at room temperature overnight
  3. extractionthe mixture is extracted with DCM (3×10 mL)
  4. concentrationAfter concentration the crude product
  5. customis purified on reverse phase HPLC (H2O/MeCN gradient)

출처 및 근거

ORD 기록
ord-9dba909da1734a5288f9b1aeb9070b87
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07820705B2

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