Dimethylformamide → (S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-3-[(S)-1-(4-trimethylsilylethynyl-phenyl)-ethyl]-[1,3]oxazinan-2-one

HRID 333911노트

반응식

HRID 333911 반응식
CCN(CC)CC.[CH3:8][Si:9]([C:12]#[CH:13])([CH3:11])[CH3:10].Br[C:15]1[CH:20]=[CH:19][C:18]([CH:21]([N:23]2[CH2:28][CH2:27][C@:26]([CH2:35][C:36]([OH:39])([CH3:38])[CH3:37])([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[O:25][C:24]2=[O:40])[CH3:22])=[CH:17][CH:16]=1.CN(C)C=O>[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C.O>[OH:39][C:36]([CH3:37])([CH3:38])[CH2:35][C@@:26]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:25][C:24](=[O:40])[N:23]([C@H:21]([C:18]2[CH:17]=[CH:16][C:15]([C:13]#[C:12][Si:9]([CH3:11])([CH3:10])[CH3:8])=[CH:20][CH:19]=2)[CH3:22])[CH2:28][CH2:27]1

참가 물질

9

반응물 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 66869824(S)-3-[1-(4-bromo-phenyl)-ethyl]-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-[1,3]oxazinan-2-one

생성물 1

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

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
90 °C

실험 절차

CuI (0.18 g), Pd(PPh3)2Cl2 (0.33 g), and NEt3 (2.22 mL) were added successively to a flask charged with a stir bar, trimethylsilylacetylene (1.31 mL), (S)-3-[1-(4-bromo-phenyl)-ethyl]-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-[1,3]oxazinan-2-one (2.00 g), and N,N-dimethylformamide (15 mL) and kept at room temperature under argon atmosphere. The flask was tightly sealed and the mixture was heated to 90° C. The mixture was stirred at 90° C. overnight and then cooled to ambient temperature. Water (80 mL) and ethyl acetate (200 mL) were added and the resulting mixture was filtered over Celite. The organic phase of the filtrate was separated and washed with brine and dried (MgSO4). The solvent was evaporated and the residue was chromatographed on silica gel (cyclohexane/ethyl acetate 3:1->0:1) to afford the title compound as an oil. Yield: 0.27 g (34% of theory); LC-MS (Method 1): tR=4.27 min; Mass spectrum (ESI+): m/z=450 [M+H]+.

후처리

  1. additioncharged with a stir bar
  2. customkept at room temperature under argon atmosphere
  3. customThe flask was tightly sealed
  4. temperaturecooled to ambient temperature
  5. filtrationthe resulting mixture was filtered over Celite
  6. customThe organic phase of the filtrate was separated
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. customThe solvent was evaporated
  10. customthe residue was chromatographed on silica gel (cyclohexane/ethyl acetate 3:1->0:1)

출처 및 근거

ORD 기록
ord-8d7fa0c896144992a1e9e69fae94dd81
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883778B2

반응 노트

불러오는 중…