Methyl iodide → (4S,5S)-tert-butyl 5-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyl-4-((2-methylthiazol-4-yl)methyl)oxazolidine-3-carboxylate

HRID 20019노트

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HRID 20019 반응식
[Si:1]([O:8][CH2:9][C@H:10]1[O:14][C:13]([CH3:16])([CH3:15])[N:12]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:11]1[CH2:24][C:25]1[N:26]=[CH:27][S:28][CH:29]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:30]([Li])CCC.IC>C1COCC1>[Si:1]([O:8][CH2:9][C@H:10]1[O:14][C:13]([CH3:15])([CH3:16])[N:12]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[C@H:11]1[CH2:24][C:25]1[N:26]=[C:27]([CH3:30])[S:28][CH:29]=1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 67270188(4S,5S)-tert-butyl 5-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyl-4-(thiazol-4-ylmethyl)oxazolidine-3-carboxylateHCID 178418339Butyllithium

생성물 1

HCID 67270237(4S,5S)-tert-butyl 5-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyl-4-((2-methylthiazol-4-yl)methyl)oxazolidine-3-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-50 °C

실험 절차

(4S,5S)-Tert-butyl 5-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyl-4-(thiazol-4-ylmethyl)oxazolidine-3-carboxylate (0.100 g, 0.23 mmol) was dissolved in THF (2.5 mL) and cooled to −78° C. n-Butyllithium (0.12 ml, 0.29 mmol) was added and the reaction was stirred at −50° C. for 40 minutes followed by the addition of iodomethane (0.018 ml, 0.29 mmol). After stirring 40 minutes the reaction was quenched with saturated ammonium chloride and extracted with ethyl acetate. The combined organic layers were washed with water, brine, and dried over sodium sulfate to afford the title compound. MS m/z: 457.3 (M+1).

후처리

  1. additionwas added
  2. stirringAfter stirring 40 minutes the reaction
  3. customwas quenched with saturated ammonium chloride
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers were washed with water, brine
  6. dry with materialdried over sodium sulfate

출처 및 근거

ORD 기록
ord-a2273b555cf44b9aa5d4e31d1a9b6cbe
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745484B2

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