반응식
C([O:8][C:9](=[O:21])[NH:10][C:11]1C=CC2OCC[O:18][C:13]=2[CH:12]=1)C1C=CC=CC=1.[Li][CH2:23]CCC.[C:27]([O:32][CH2:33][C@H:34]1[O:36][CH2:35]1)(=O)[CH2:28][CH2:29][CH3:30].C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1.CC(=O)OCC>[O:32]1[C:27]2[CH:28]=[CH:29][C:30]([N:10]3[CH2:11][C@@H:12]([CH2:13][OH:18])[O:8][C:9]3=[O:21])=[CH:23][C:35]=2[O:36][CH2:34][CH2:33]1참가 물질
7
반응물 4
생성물 1
시약·촉매·용매 2
반응 조건
- 온도
- -78 °C
실험 절차
A solution of (2,3-dihydro-benzo[1,4]dioxin-6-yl)-carbamic acid benzyl ester (13.0 g, 45.6 mmol) in THF (220 mL) was cooled to −78° C. before the dropwise addition of n-BuLi (29.5 mL of a 2.3M solution in Hex, 1.1 eq.). The mixture was stirred at −78° C. for 1 h and then warmed to −15° C. and treated dropwise with (S)-glycidyl butyrate (7.37 g, 1.1 eq.). The mixture was stirred at rt overnight. Cs2CO3 (tip of a spatula) was added and the mixture heated at 40° C. until complete conversion. The mixture was diluted with EA and washed with a sat. aq. NH4Cl and water. The org. layer was dried over MgSO4 and concentrated. The residue was purified by CC (Hex/EA 2:1, 1:1) to afford the title intermediate as a grey solid (7.04 g, 62% yield).
후처리
- temperaturewarmed to −15° C.
- stirringThe mixture was stirred at rt overnight
- temperaturethe mixture heated at 40° C. until complete conversion
- washwashed with a sat. aq. NH4Cl and water
- dry with materiallayer was dried over MgSO4
- concentrationconcentrated
- customThe residue was purified by CC (Hex/EA 2:1, 1:1)
출처 및 근거
- ORD 기록
- ord-ebc6cbc2312542c297719b5630668218
- 출처 데이터셋
- uspto-grants-2016_05
- 특허 번호
- US09346804B2
연결된 노트
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