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Triphenylphosphine → tert-butyl [(1S)-2-(4-bromo-3,5-difluorophenoxy)-1-methylethyl]carbamate

HRID 1026361
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HRID 1026361 반응식
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[F:10].O[CH2:12][C@@H:13]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH3:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([O:9][CH2:14][C@@H:13]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:21])[CH3:20])[CH3:12])=[CH:4][C:3]=1[F:10]
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참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 70231031,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamateHCID 71720274-Bromo-3,5-difluorophenol

생성물 1

HCID 86666328tert-butyl [(1S)-2-(4-bromo-3,5-difluorophenoxy)-1-methylethyl]carbamate수율 58.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

To a solution of 4-bromo-3,5-difluorophenol (5.0 g), tert-butyl [(1S)-2-hydroxy-1-methylethyl]carbamate (5 g) and triphenylphosphine (7.5 g) in THF (50 mL) was added diisopropyl azodicarboxylate (1.9 M in toluene, 14 mL) dropwise at room temperature. The reaction mixture was stirred at 60° C. overnight and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to afford the title compound (5.1 g).

후처리

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-24623d532f0e450686ee1f9d209ae015
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08729102B2

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