1,1-Dichloroethane → 3-Cyclohexyl-N-(3,3-dimethyl-butyl)-3-[(5-nitro-2-phenoxy-pyridin-4-ylmethyl)-amino]-propionamide

HRID 491912Notes

Reaction equation

HRID 491912 reaction equation
[NH2:1][CH:2]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[CH2:3][C:4]([NH:6][CH2:7][CH2:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:5].[N+:19]([C:22]1[C:23]([CH:35]=O)=[CH:24][C:25]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[N:26][CH:27]=1)([O-:21])=[O:20].ClC(Cl)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>[OH-].[Na+]>[CH:13]1([CH:2]([NH:1][CH2:35][C:23]2[C:22]([N+:19]([O-:21])=[O:20])=[CH:27][N:26]=[C:25]([O:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:24]=2)[CH2:3][C:4]([NH:6][CH2:7][CH2:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:5])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

6

Reactant 4

HCID 63651,1-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 576783284-Formyl-5-nitro-2-phenoxypyridineHCID 670237583-Amino-3-cyclohexyl-N-(3,3-dimethyl-butyl)-propionamide

Product 1

HCID 670235503-Cyclohexyl-N-(3,3-dimethyl-butyl)-3-[(5-nitro-2-phenoxy-pyridin-4-ylmethyl)-amino]-propionamide

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture 3-amino-3-cyclohexyl-N-(3,3-dimethyl-butyl)-propionamide (0.57 g, 2.24 mmol), 5-nitro-2-phenoxy-pyridine-4-carbaldehyde (0.57 g, 2.35 mmol), and dichloroethane (100 mL) was stirred for 12 hrs. Sodium triacetoxyborohydride (1.09 g, 5.15 mmol) was added and the resulting mixture was stirred 4 hours at room temperature. Sodium hydroxide solution ([0.1N], 100 mL) was added, the organic layer was separated, treated with MgSO4, filtered and the solvent evaporated under reduced pressure to yield an oil. The oil was purified by column chromatography (10%-40% ethyl acetate/heptane) to yield a residue.

Workup

  1. customthe organic layer was separated
  2. additiontreated with MgSO4
  3. filtrationfiltered
  4. customthe solvent evaporated under reduced pressure
  5. customto yield an oil
  6. customThe oil was purified by column chromatography (10%-40% ethyl acetate/heptane)
  7. customto yield a residue

Sources & evidence

ORD record
ord-60324abc090d432a90be748da0c0d905
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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