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

HRID 491912ノート

反応式

HRID 491912 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-60324abc090d432a90be748da0c0d905
出典データセット
uspto-grants-2009_05
特許番号
US07531545B2

反応ノート

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