Tributyl borate → 3-(1-Carboxy-ethyl)-phenyl boronic acid

HRID 216177

반응식

HRID 216177 반응식
Br[C:2]1[CH:3]=[C:4]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.C([Li])(C)(C)C.[B:18](OCCCC)([O:24]CCCC)[O:19]CCCC>CCOCC>[C:9]([CH:8]([C:4]1[CH:3]=[C:2]([B:18]([OH:24])[OH:19])[CH:7]=[CH:6][CH:5]=1)[CH3:12])([OH:11])=[O:10]

참가 물질

5

반응물 3

HCID 12712Tributyl borateHCID 127979542-(3-Bromophenyl)propanoic acid2회HCID 178418306HCID 178418306, 화합물

생성물 1

HCID 576360703-(1-Carboxy-ethyl)-phenyl boronic acid

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

A solution of 2-(3-bromo-phenyl)-propionic acid [500 mg, 2.18 mmol, Intermediate (69)] in anhydrous ether (20 mL) is added tert-butyl lithium (1.7 M in pentane, 5.4 mL, 9.16 mmol) dropwise at −78° C. and this mixture is stirred for 30 minutes treated with tributyl borate (2.34 mL, 8.72 mmol). The reaction mixture is allowed to warm up to room temperature, stirred for 15 hours, diluted with ether, and quenched with 1 M H3PO4. After stirring for 30 minutes the ether layer is separated and extracted three times with 2 N sodium hydroxide (20 mL). The combined sodium hydroxide extracts are acidified with 6 N hydrochloric acid to pH=1 and extracted three times with ether (50 mL). The combined organic extracts are washed with brine, dried over sodium sulfate and concentrated to obtain 3-(1-carboxy-ethyl)-phenyl boronic acid [Intermediate (70)] as a solid, which is used without further purification.

후처리

  1. stirringstirred for 15 hours
  2. customquenched with 1 M H3PO4
  3. stirringAfter stirring for 30 minutes the ether layer
  4. customis separated
  5. extractionextracted three times with 2 N sodium hydroxide (20 mL)
  6. extractionextracted three times with ether (50 mL)
  7. washThe combined organic extracts are washed with brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-33babe47ffbc4957a900b1aba4e92a00
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193183B2

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