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tert-Butyl methyl ether → Tert-butyl 2,2-dimethyl-4-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexyl]butyrate

HRID 854671
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HRID 854671 반응식
[OH:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][C@H:4]([CH2:8][CH2:9][C:10]([CH3:19])([CH3:18])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3]1.I[CH2:21][C:22]1[N:23]=[C:24]([C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=2)[O:25][C:26]=1[CH3:27].[H-].[Na+].C(OC)(C)(C)C>CN(C)C=O>[CH3:18][C:10]([CH3:19])([CH2:9][CH2:8][C@H:4]1[CH2:5][CH2:6][CH2:7][C@@H:2]([O:1][CH2:21][C:22]2[N:23]=[C:24]([C:28]3[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=3)[O:25][C:26]=2[CH3:27])[CH2:3]1)[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 15413tert-Butyl methyl etherHCID 24758Sodium hydrideHCID 219803112-(4-Methylphenyl)-4-iodomethyl-5-methyloxazoleHCID 69244301Tert-butyl 4-(cis-3-hydroxycyclohexyl)-2,2-dimethylbutyrate

생성물 1

HCID 69244352Tert-butyl 2,2-dimethyl-4-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexyl]butyrate

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

365 mg of tert-butyl 4-(cis-3-hydroxycyclohexyl)-2,2-dimethylbutyrate are, together with 850 mg of 4-iodomethyl-5-methyl-2-(4 methylphenyl)oxazole, dissolved in 5 ml of dimethylformamide, and 110 mg of sodium hydride (60% strength in paraffin) are added. After 1 hour of stirring at room temperature, 100 ml of methyl tert-butyl ether are added and the reaction mixture is washed three times with water. The organic phase is dried over MgSO4 and the solvent is then removed under reduced pressure. The residue is purified by RP-HPLC. This gives 330 mg of tert-butyl 2,2-dimethyl-4-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexyl]butyrate as a white solid. C28H41NO4 (455.64), MS(ESI): 456 (M+H+).

후처리

  1. washthe reaction mixture is washed three times with water
  2. dry with materialThe organic phase is dried over MgSO4
  3. customthe solvent is then removed under reduced pressure
  4. customThe residue is purified by RP-HPLC

출처 및 근거

ORD 기록
ord-01f2fd27367148969257483291a1044d
출처 데이터셋
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07259177B2

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