Sodium hydride → ethyl 6-[4-[N-(4-pyridyl)-N-tertiary-butyloxycarbonylamino]phenoxy]hexanoate

HRID 1291887

反応式

HRID 1291887 の反応式
[H-].[Na+].[N:3]1[CH:8]=[CH:7][C:6]([N:9]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:5][CH:4]=1.Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>CN(C=O)C>[N:3]1[CH:8]=[CH:7][C:6]([N:9]([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:21][CH:22]=2)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 117544Ethyl 6-bromohexanoateHCID 18918286tert-butyl N-(4-hydroxyphenyl)-N-(pyridin-4-yl)carbamate

生成物 1

HCID 18918347ethyl 6-[4-[N-(4-pyridyl)-N-tertiary-butyloxycarbonylamino]phenoxy]hexanoate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Sodium hydride (50% w/w dispersion in mineral oil, 55 mg) was added under argon to a stirred solution of the product from step (iii) above (300 mg) in dry DMF (5 ml). After five minutes, ethyl 6-bromohexanoate (0.20 ml) was added and the mixture stirred for 16 hours. The DMF was evaporated in vacuo and the residue partitioned between dichloromethane and water. The aqueous phase was extracted with further dichloromethane. The combined organic extracts were washed with water then dried, and evaporated. The residue was purified by chromatography on alumina, eluting with dichloromethane and then 1% v/v methanol/dichloromethane. Evaporation of the appropriate fractions gave ethyl 6-[4-[N-(4-pyridyl)-N-tertiary-butyloxycarbonylamino]phenoxy]hexanoate, 260 mg, as a yellow gum: NMR (CDCl3) δ 8.40 (2H, dd), 7.16 (2H, dd), 7.07 (2H, m), 6.90 (2H, m), 4.13 (2H, q), 3.98 (2H, t), 2.34 (2H, t), 1.78 (4H, m), 1.57 (2H, m), 1.44 (9H, s), 1.26 (3H, t); m/e 429 (M+H)+.

後処理

  1. customThe DMF was evaporated in vacuo
  2. customthe residue partitioned between dichloromethane and water
  3. extractionThe aqueous phase was extracted with further dichloromethane
  4. washThe combined organic extracts were washed with water
  5. customthen dried
  6. customevaporated
  7. customThe residue was purified by chromatography on alumina
  8. washeluting with dichloromethane
  9. customEvaporation of the appropriate fractions

出典と根拠

ORDレコード
ord-ed8ffab027e54013ada2adc638e0a2c7
出典データセット
uspto-grants-1998_05
特許番号
US05753659

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