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

HRID 2070997ノート

反応式

HRID 2070997 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-828b64a114824c14aa99835590cde541
出典データセット
uspto-grants-2012_10
特許番号
US08299267B2

反応ノート

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