Imidazole → tert-butyl N-[(1R)-1-[4-(iodomethyl)-1,3-oxazol-2-yl]ethyl]carbamate

HRID 2070997노트

반응식

HRID 2070997 반응식
[I:1]I.N1C=CN=C1.O[CH2:9][C:10]1[N:11]=[C:12]([C@H:15]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH3:16])[O:13][CH:14]=1>C(Cl)Cl>[I:1][CH2:9][C:10]1[N:11]=[C:12]([C@H:15]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH3:16])[O:13][CH:14]=1

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 807IodineHCID 68670262(R)-tert-butyl 1-(4-(hydroxymethyl)oxazol-2-yl)ethylcarbamate

생성물 1

HCID 68670282tert-butyl N-[(1R)-1-[4-(iodomethyl)-1,3-oxazol-2-yl]ethyl]carbamate수율 84%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of TPP (873 mg, 3.33 mmol) in CH2Cl2 (10 mL), was added I2 (845 mg, 3.33 mmol), and stirred for 10 min. Imidazole (227 mg, 3.33 mmol) was added and stirred for an additional 10 min and then a solution of (R)-tert-butyl 1-(4-(hydroxymethyl)oxazol-2-yl)ethylcarbamate (537 mg, 2.22 mmol) in CH2Cl2 (15 mL) was added. After 2 h, the reaction mixture was washed successively with sat. aq. NaHCO3, aq. Na2S2O3, dried on Na2SO4 and concentrated under low pressure. The residue was chromatographed on silica gel (20% ethyl acetate/80% hexanes) to yield 84% of (R)-tert-butyl 1-(4-(iodomethyl)oxazol-2-yl)ethylcarbamate.

후처리

  1. stirringstirred for an additional 10 min
  2. waitAfter 2 h
  3. washthe reaction mixture was washed successively with sat. aq. NaHCO3, aq. Na2S2O3
  4. customdried on Na2SO4
  5. concentrationconcentrated under low pressure
  6. customThe residue was chromatographed on silica gel (20% ethyl acetate/80% hexanes)

출처 및 근거

ORD 기록
ord-828b64a114824c14aa99835590cde541
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299267B2

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