Tetrabutylammonium Fluoride → (S)-3-((S)-1-(4-ethynylphenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one

HRID 333910

반응식

HRID 333910 반응식
[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].[OH:19][C:20]([CH3:50])([CH3:49])[CH2:21][C@@:22]1([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[O:27][C:26](=[O:28])[N:25]([C@H:29]([C:31]2[CH:36]=[CH:35][C:34]([C:37]#[C:38][Si](C)(C)C)=[CH:33][CH:32]=2)[CH3:30])[CH2:24][CH2:23]1>O1CCCC1>[C:37]([C:34]1[CH:33]=[CH:32][C:31]([C@@H:29]([N:25]2[CH2:24][CH2:23][C@:22]([CH2:21][C:20]([OH:19])([CH3:49])[CH3:50])([C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)[O:27][C:26]2=[O:28])[CH3:30])=[CH:36][CH:35]=1)#[CH:38]

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 66869815(S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-3-[(S)-1-(4-trimethylsilylethynyl-phenyl)-ethyl]-[1,3]oxazinan-2-one

생성물 1

HCID 86670541(S)-3-((S)-1-(4-ethynylphenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

nBu4NF (1 mol/L in tetrahydrofuran, 4.90 mL) was added to a solution of (S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-3-[(S)-1-(4-trimethylsilylethynyl-phenyl)-ethyl]-[1,3]oxazinan-2-one (2.00 g) in tetrahydrofuran (20 mL) at room temperature. The solution was stirred for 1 h at room temperature and then concentrated under reduced pressure. Ethyl acetate was added to the residue and the resulting mixture was washed with water and brine. The organic phase was dried (MgSO4) and the solvent was evaporated to afford the title compound as an oil that solidified on standing. Yield: 1.60 g (95% of theory); LC-MS (Method 1): tR=3.64 min; Mass spectrum (ESI+): m/z=378 [M+H]+.

후처리

  1. concentrationconcentrated under reduced pressure
  2. additionEthyl acetate was added to the residue
  3. washthe resulting mixture was washed with water and brine
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-c901cdf00d444534b545e4aa3499ab88
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883778B2

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