Benzyl Bromide → (s)-Methyl 2-(4-(benzyloxymethyl)-6-methylpyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropanoate

HRID 1513208노트

반응식

HRID 1513208 반응식
[H-].[Li+].[OH:3][CH2:4][C:5]1[CH:10]=[C:9]([CH3:11])[N:8]=[C:7]([O:12][C@@H:13]([C:18]([O:31][CH3:32])([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:14]([O:16][CH3:17])=[O:15])[N:6]=1.[CH2:33](Br)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>O1CCCC1.CN(C)C=O>[CH2:33]([O:3][CH2:4][C:5]1[CH:10]=[C:9]([CH3:11])[N:8]=[C:7]([O:12][C@@H:13]([C:18]([O:31][CH3:32])([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:14]([O:16][CH3:17])=[O:15])[N:6]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

참가 물질

6

반응물 3

HCID 7498Benzyl BromideHCID 62714Lithium hydrideHCID 59441450(S)-Methyl 2-(4-(hydroxymethyl)-6-methylpyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropanoate

생성물 1

HCID 59441452(s)-Methyl 2-(4-(benzyloxymethyl)-6-methylpyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropanoate수율 69%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

To a 0° C. mixture of lithium hydride (0.235 g, 29.4 mmol) in tetrahydrofuran and dimethylformamide (30 mL: 10 mL) is added the compound of Example 11 (3.0 g, 7.3 mmol) and the mixture stirred for 0.5 hr. Benzyl bromide (1.257 g, 7.3 mmol) is then added and the reaction stirred 12 hr at room temperature. The reaction is poured into ice-water (100 mL) and the quenched mixture extracted with ethyl acetate (2×100 mL). Concentration gives crude product that is purified by column chromatography on silica gel eluted with ethyl acetate-hexane (1:9) to yield the title compound (2.5 g, 69%). MS m/z 499.0 (M+.1).

후처리

  1. stirringthe reaction stirred 12 hr at room temperature
  2. extractionthe quenched mixture extracted with ethyl acetate (2×100 mL)
  3. concentrationConcentration
  4. customgives crude product that
  5. customis purified by column chromatography on silica gel
  6. washeluted with ethyl acetate-hexane (1:9)

출처 및 근거

ORD 기록
ord-25927e589e3d40abaa1dc3171ca0a158
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08217155B2

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