3-Hydroxypyridine → ethyl 8-[N-(p-chlorophenylsulfonyl)-N-(t-butoxycarbonyl)-amino]-4-[2-(3-pyridyloxy)ethyl]-octanoate

HRID 1494156Notes

Reaction equation

HRID 1494156 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:19][CH2:20][CH2:21][CH2:22][CH:23]([CH2:31][CH2:32]I)[CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH:34][C:35]1[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=1.CC(C)([O-])C.[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:19][CH2:20][CH2:21][CH2:22][CH:23]([CH2:31][CH2:32][O:34][C:35]2[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=2)[CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 79713-HydroxypyridineHCID 14986720ethyl 8-[N-(p-chlorophenylsulfonyl)-N-(t-butoxycarbonyl)amino]-4-(2-iodoethyl)-octanoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 14986717ethyl 8-[N-(p-chlorophenylsulfonyl)-N-(t-butoxycarbonyl)-amino]-4-[2-(3-pyridyloxy)ethyl]-octanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 3.1 g (5 mmol) of ethyl 8-[N-(p-chlorophenylsulfonyl)-N-(t-butoxycarbonyl)amino]-4-(2-iodoethyl)octanoate in 10 ml dimethylformamide at 0° C. under an inert atmosphere is added a solution of 0.62 g (6.5 mmol) 3-hydroxypyridine and 0.73 g potassium-t-butoxide in 20 ml dimethylformamide, dropwise. After 24 hours at room temperature the reaction is evaporated to dryness. The residue is dissolved in ethyl acetate and the solution is washed with cold 5% Na2CO3 solution and brine, dried and evaporated to yield ethyl 8-[N-(p-chlorophenylsulfonyl)-N-(t-butoxycarbonyl)-amino]-4-[2-(3-pyridyloxy)-ethyl]-octanoate.

Workup

  1. customAfter 24 hours at room temperature the reaction is evaporated to dryness
  2. dissolutionThe residue is dissolved in ethyl acetate
  3. washthe solution is washed with cold 5% Na2CO3 solution and brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-593c389c736d427ca5b8dd63f7a6cd2b
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

Loading…