Sodium Carbonate → HCID 178489343, 화합물

HRID 2196568노트

반응식

HRID 2196568 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]([CH:32]=[CH:33][CH:34]=2)[CH2:12][N:13]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:14][CH2:15][N:16]([CH3:24])C(=O)OC(C)(C)C)O1.Br[C:37]1[CH:53]=[C:52]([CH3:54])[C:40]2[NH:41][C:42]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=3[O:50][CH3:51])=[N:43][C:39]=2[CH:38]=1.[C:55](=[O:58])([O-])[O-:56].[Na+].[Na+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:51][O:50][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=1[C:42]1[NH:41][C:40]2[C:52]([CH3:54])=[CH:53][C:37]([C:9]3[CH:10]=[C:11]([CH:32]=[CH:33][CH:34]=3)[CH2:12][N:13]([CH2:14][CH2:15][NH:16][CH2:24][C:55]([O:56][C:11]([CH3:32])([CH3:12])[CH3:10])=[O:58])[C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[CH:38][C:39]=2[N:43]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 69095178HCID 69095178, 화합물HCID 178489342HCID 178489342, 화합물

생성물 1

HCID 178489343HCID 178489343, 화합물수율 97%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
80 °C

실험 절차

To a solution of 158 (0.165 g, 0.336 mmol) in DME (1.5 mL) and water (0.5 mL) was added 159 (0.107 g, 0.336 mmol), sodium carbonate (0.107 g, 1.009 mmol) followed by Pd(Ph3P)4 (0.025 g, 0.022 mmol). The reaction mixture was degassed with nitrogen and heated to 80° C. for 16 hours. After the usual work-up the crude material was purified by silica gel chromatography (Biotage 25M, 20 to 30 to 50% ethyl acetate in hexanes) to give 160 (97.7 mg, 0.163 mmol, 48.3% yield) as yellow crusty solid. LRMS (ESI): (calc.) 600.7 (found) 601.5 (MH)+.

후처리

  1. customThe reaction mixture was degassed with nitrogen
  2. customAfter the usual work-up the crude material was purified by silica gel chromatography (Biotage 25M, 20 to 30 to 50% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-0cd01431ac83472a80fa748e2e439786
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338437B2

반응 노트

불러오는 중…