Potassium Iodide → Methyl 2-(3-tert-Butoxycarbonylaminopropoxy)-4-tert-butylbenzoate

HRID 644289노트

반응식

HRID 644289 반응식
[C:1]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([OH:15])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:16]([NH:23][CH2:24][CH2:25][CH2:26]Br)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].[I-].[K+]>CN(C=O)C>[C:19]([O:18][C:16]([NH:23][CH2:24][CH2:25][CH2:26][O:15][C:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10])=[O:17])([CH3:22])([CH3:21])[CH3:20]

참가 물질

5

반응물 3

HCID 4875Potassium IodideHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 20777194Methyl 4-tert-butyl-2-hydroxybenzoate

생성물 1

HCID 68530190Methyl 2-(3-tert-Butoxycarbonylaminopropoxy)-4-tert-butylbenzoate수율 45.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

Methyl 4-tert-butyl-2-hydroxybenzoate (2.41 g, 11.6 mmol) was dissolved in DMF (15 mL) and K2 CO3 (2.39 g, 17.4 mmol) and N-Boc-3-bromopropylamine (4.14 g, 17.4 mmol) was added using DMF (10 mL) to aid the transfer. Potassium iodide (0.30 g) was added, and the reaction stirred at room temperature under nitrogen for 18 hr. The DMF was removed in vacuo and the residue taken up in ethyl acetate and washed with water and brine, dried, and the solvent removed in vacuo to give a viscous brown oil. Purification by chromaotgraphy over silica on a preparative scale apparatus, eluting with a gradient of hexane to hexane:ethyl acetate (70:30) gave 1.91 g (45.2%) of a viscous yellow oil.

후처리

  1. customThe DMF was removed in vacuo
  2. washwashed with water and brine
  3. customdried
  4. customthe solvent removed in vacuo
  5. customto give a viscous brown oil
  6. customPurification by chromaotgraphy over silica on a preparative scale apparatus
  7. washeluting with a gradient of hexane to hexane:ethyl acetate (70:30)

출처 및 근거

ORD 기록
ord-77670657196546109d8e761506ef5c33
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700628B2

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