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

HRID 266758Notes

Reaction equation

HRID 266758 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-75095d6f23ce408080258a4a37a945b8
Source dataset
uspto-grants-1997_07
Patent number
US05652242

Reaction notes

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