반응식
[CH:1](NC(C)C)(C)C.C([Li])CCC.[O:13]=[C:14]1[O:18][CH2:17][C@H:16]([NH:19][C:20](=[O:29])[O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:15]1.CI.[Cl-].[NH4+]>C1COCC1.CCCCCC.C[C@H]1O[C@H]2[C@H](O)[C@@H](O)[C@H](OC3C4C(=CC5OCOC=5C=4)[C@@H](C4C=C(OC)C(O)=C(OC)C=4)[C@@H]4[C@@H]3COC4=O)O[C@@H]2CO1.C1COP(NCCCl)(=O)N(CCCl)C1.[NH2-].[NH2-].Cl[Pt+2]Cl.O>[CH3:1][C@H:15]1[C:14](=[O:13])[O:18][CH2:17][C@@H:16]1[NH:19][C:20](=[O:29])[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1참가 물질
반응물 5
생성물 1
시약·촉매·용매 4
반응 조건
- 온도
- 0 °C
실험 절차
272 μl (1.9 mmol) diisopropylamine are placed in 3 ml THF and while cooling with ice 1.2 ml (1.9 mmol) of an n-butyllithium solution in hexane (1.6M) are added. The mixture is stirred for 10 minutes at 0° C., then cooled to −78° C. and a solution of 200 mg (0.85 mmol) benzyl (R)-(5-oxo-tetrahydrofuran-3-yl)-carbamate in 1 ml THF is added dropwise. The mixture is stirred for one hour at −78° C. Then 210 μl (3.3 mmol) methyl iodide are added dropwise, and the mixture is heated to −60° C. within one hour. Then 0.5 ml sat. ammonium chloride solution is added and the mixture is heated to ambient temperature. Water is added and the mixture is extracted three times with ethyl acetate. The combined organic phases are dried over sodium sulphate and evaporated to dryness. The residue is taken up in DMF, acidified with TFA and purified by reversed-phase chromatography.
후처리
- temperaturecooled to −78° C.
- stirringThe mixture is stirred for one hour at −78° C
- temperaturethe mixture is heated to −60° C. within one hour
- temperaturethe mixture is heated to ambient temperature
- extractionthe mixture is extracted three times with ethyl acetate
- dry with materialThe combined organic phases are dried over sodium sulphate
- customevaporated to dryness
- custompurified by reversed-phase chromatography
출처 및 근거
- ORD 기록
- ord-5b312c38ffbe4103ae25f7061656ab9e
- 출처 데이터셋
- uspto-grants-2009_11
- 특허 번호
- US07615549B2
연결된 노트
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